Reaxys
PubChem
eMolecules
Bioactivities (401)
Yield
LabNetwork
SigmaAldrich
Reactions (276)
Conditions
Substances (252)
Targets (66)
Citations (72)
References
100
Synthesize Find similar
Rx-ID: 22949123 Find similar reactions
SUVEN LIFE SCIENCES LIMITED
Patent: WO2004/48330 A1, 2004 ; Location in patent: Page 55 ; Title/Abstract Full Text Show Details
101
Synthesize Find similar
Rx-ID: 6845820 Find similar reactions
5-Nitro-indol, Formaldehyd, N-Benzyl-piperazin, wss. Essigsaeure, Mannich-Rk. nach Meth. v. G. Cavallini, F. Ravenna, Farmaco (Pavia), Ed. Sci. 13 (1958) 105;
DeGraw; Brown; Skinner
Journal of medicinal chemistry, 1966 , vol. 9, # 1 p. 140 - 142 Title/Abstract Full Text View citing articles Show Details
(yield)9percent;
DeGraw; Brown; Skinner
Journal of medicinal chemistry, 1966 , vol. 9, # 1 p. 140 - 142 Title/Abstract Full Text View citing articles Show Details
102
Synthesize Find similar
Rx-ID: 8742473 Find similar reactions
52%
With acetic acid in dichloromethane
T=20°C; Mannich reaction; 6 h;
Synthesize Find similar
Synthesize Find similar
Synthesize Find similar
Huebner; Kraxner; Gmeiner
Journal of Medicinal Chemistry, 2000 , vol. 43, # 23 p. 4563 - 4569 Title/Abstract Full Text View citing articles Show Details
103
Synthesize Find similar
Rx-ID: 8742474 Find similar reactions
51%
104
With acetic acid in dichloromethane
T=20°C; Mannich reaction; 6 h;
Synthesize Find similar
Synthesize Find similar
Huebner; Kraxner; Gmeiner
Journal of Medicinal Chemistry, 2000 , vol. 43, # 23 p. 4563 - 4569 Title/Abstract Full Text View citing articles Show Details
Synthesize Find similar
Synthesize Find similar
Rx-ID: 22949104 Find similar reactions
SUVEN LIFE SCIENCES LIMITED
Patent: WO2004/48330 A1, 2004 ; Location in patent: Page 52-53 ;
Title/Abstract Full Text Show Details
105
Synthesize Find similar
Rx-ID: 33537481 Find similar reactions
Synthesize Find similar
Synthesize Find similar
Synthesize Find similar
80%
in water
Mannich reaction; 2 h; Reflux;
Khan, Khalid Mohammed; Rahim, Fazal; Ambreen, Nida; Taha, Muhammad; Iqbal, Sarosh; Haider, Syed Moazzam; Perveen, Shahnaz
Journal of the Chemical Society of Pakistan, 2012 , vol. 34, # 3 p. 748 - 757 Title/Abstract Full Text View citing articles Show Details
in water
2 h; Reflux; Hide Experimental Procedure
Mesaik, M. Ahmed; Khan, Khalid Mohammed; Rahim, Fazal; Taha, Muhammad; Haider, Syed Moazzam; Perveen, Shahnaz; Khalid, Ahmed Shukralla; Abdalla, Omer M.; Soomro, Samreen; Voelter, Wolfgang
Bioorganic Chemistry, 2015 , vol. 60, p. 118 - 122 Title/Abstract Full Text View citing articles Show Details
5:
General procedure: Indole (3mmol), formaldehyde (1.2mmol), and secondary amine (3mmol), mL were mixed in reaction flask and then add distill water 10–15 and refluxed the solution for 2h with vigorous stirring. The reaction completion was checked by TLC, and the resulting solid mixture was then filter. In some cases solid mixture was not formed so it was extracted with ethyl acetate, purified by column chromatography using acetone and hexane system in 1:1 ratio, and pure product is obtained in 75–89percent yield [37].
106
Synthesize Find similar
Rx-ID: 5950905 Find similar reactions
Amin 7, p-Fluor-benzoylchlorid, NEt3;
Glamkowski et al.
Journal of Medicinal Chemistry, 1977 , vol. 20, p. 1485 Full Text View citing articles Show Details
Entspr. NH-Verb., Acyl.;
Hoechst
Patent: FR2272673DE2522143 , 1975 ; Chem.Abstr., vol. 84, # 90183 Full Text Show Details
107
Synthesize Find similar
Rx-ID: 9577804 Find similar reactions
20%
in acetic acid
T=20°C; Mannich reaction; 3 h;
Synthesize Find similar
Synthesize Find similar
Synthesize Find similar
Malinka, Wieslaw; Swiatek, Piotr
Acta Poloniae Pharmaceutica - Drug Research, 2004 , vol. 61, # 2 p. 107 - 111 Title/Abstract Full Text View citing articles Show Details
108
Synthesize Find similar
Rx-ID: 36054896 Find similar reactions
58%
in acetic acid
T=0°C; 1 h; Hide Experimental Procedure
Synthesize Find similar
Synthesize Find similar
Synthesize Find similar
Abdelfattah, Mohamed A.O.; Lehmann, Jochen; Abadi, Ashraf H.
Bioorganic and Medicinal Chemistry Letters, 2013 , vol. 23, # 18 p. 5077 - 5081 Title/Abstract Full Text View citing articles Show Details
General procedure: 10 mmol (1.17 gm) of indoletogether with 10 mmol of the corresponding phenyl piperazine free base and 15mL of HCHO 37percent were mixed with 5 mL glacial acetic acid at 0Oc for 1hour. The mixture was then alkalinized with 5M NaOH and extracted twice with 30mL diethyl ether. The combined organic layers were dried over anhydrous Na2SO4and evaporated under reduced pressure. The crude residue was then subjected toSilica gel column chromatography eluting with CH2Cl2:MeOH 9.5: 0.5. 4Yield:(2.1 gm, 58percent); m.p.: 49-51 oC; 1HNMR (CDCl3):2.06 (brs, 4H, 2 X –CH2, piperazine), 2.28 (brs, 4H, 2 X –CH2,
piperazine),3.84 (s, 2H, -CH2-), 6.93- 7.79 (m, 8H, Aromatic), 8.24 (brs, 1H, NH); GC/MS:m/z 360 (M+, 5percent), 206 (40percent), 231 (80percent), 120 (100percent), 77 (40percent); CHN: for C19H19Cl2N3calcd. C 63.34, H 5.32, N 11.66 ; found C 63.73; H 5.65; N 12.01.
109
Synthesize Find similar
Rx-ID: 40641134 Find similar reactions
in water; acetonitrile
0.266667 h;
Synthesize Find similar
Synthesize Find similar
Rodrigues, Tiago; Hauser, Nadine; Reker, Daniel; Reutlinger, Michael; Wunderlin, Tiffany; Hamon, Jacques; Koch, Guido; Schneider, Gisbert
Angewandte Chemie - International Edition, 2015 , vol. 54, # 5 p. 1551 - 1555 Angew. Chem., 2015 , vol. 127, # 5 p. 1571 - 1575,5 Title/Abstract Full Text View citing articles Show Details
110
Synthesize Find similar
Rx-ID: 33537477 Find similar reactions
Synthesize Find similar
Synthesize Find similar
Synthesize Find similar
81%
in water
Mannich reaction; 2 h; Reflux;
Khan, Khalid Mohammed; Rahim, Fazal; Ambreen, Nida; Taha, Muhammad; Iqbal, Sarosh; Haider, Syed Moazzam; Perveen, Shahnaz
Journal of the Chemical Society of Pakistan, 2012 , vol. 34, # 3 p. 748 - 757 Title/Abstract Full Text View citing articles Show Details
in water
2 h; Reflux; Hide Experimental Procedure
Mesaik, M. Ahmed; Khan, Khalid Mohammed; Rahim, Fazal; Taha, Muhammad; Haider, Syed Moazzam; Perveen, Shahnaz; Khalid, Ahmed Shukralla; Abdalla, Omer M.; Soomro, Samreen; Voelter, Wolfgang
Bioorganic Chemistry, 2015 , vol. 60, p. 118 - 122 Title/Abstract Full Text View citing articles Show Details
5:
General procedure: Indole (3mmol), formaldehyde (1.2mmol), and secondary amine (3mmol), mL were mixed in reaction flask and then add distill water 10–15 and refluxed the solution for 2h with vigorous stirring. The reaction completion was checked by TLC, and the resulting solid mixture was then filter. In some cases solid mixture was not formed so it was extracted with ethyl acetate, purified by column chromatography using acetone and hexane system in 1:1 ratio, and pure product is obtained in 75–89percent yield [37].
111
Synthesize Find similar
Rx-ID: 22949106 Find similar reactions
SUVEN LIFE SCIENCES LIMITED
Patent: WO2004/48330 A1, 2004 ; Location in patent: Page 52-53 ;
Title/Abstract Full Text Show Details
112
Synthesize Find similar
Rx-ID: 33307381 Find similar reactions
Synthesize Find similar
Synthesize Find similar
20%
in ethanol; water
T=20°C;
Yarim, Mine; Koksal, Meric; Schepmann, Dirk; Wuensch, Bernard
Chemical Biology and Drug Design, 2011 , vol. 78, # 5 p. 869 - 875 Title/Abstract Full Text View citing articles Show Details
20%
in ethanol; water
T=20°C; Mannich reaction;
Akkoc, Meric Koeksal; Yueksel, Mine Yarim; Durmaz, Irem; Atalay, Renguel Ecetin
Turkish Journal of Chemistry, 2012 , vol. 36, # 4 p. 515 - 525 Title/Abstract Full Text View citing articles Show Details
Synthesize Find similar
113
Synthesize Find similar
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetonitrile / 30 - 80 °C 2.1: acetic acid / 1,2-dichloro-ethane / 6 h / 30 °C / |Molecular sieve 2.2: 6 h / 0 - 30 °C View Scheme
Synthesize Find similar
Rx-ID: 43099939 Find similar reactions
Jeankumar, Variam Ullas; Reshma, Rudraraju Srilakshmi; Vats, Rahul; Janupally, Renuka; Saxena, Shalini; Yogeeswari, Perumal; Sriram, Dharmarajan
European Journal of Medicinal Chemistry, 2016 , vol. 122, p. 216 - 231 Title/Abstract Full Text View citing articles Show Details
114
Synthesize Find similar
Rx-ID: 43100020 Find similar reactions
60.5%
Synthesize Find similar
Stage #1: With acetic acid in 1,2-dichloro-ethane
T=30°C; 6 h; Molecular sieve; Stage #2: With sodium tris(acetoxy)borohydride in methanol
T=0 - 30°C; 6 h; Hide Experimental Procedure
Synthesize Find similar
Jeankumar, Variam Ullas; Reshma, Rudraraju Srilakshmi; Vats, Rahul; Janupally, Renuka; Saxena, Shalini; Yogeeswari, Perumal; Sriram, Dharmarajan
European Journal of Medicinal Chemistry, 2016 , vol. 122, p. 216 - 231 Title/Abstract Full Text View citing articles Show Details
4.1.7 General procedure for the synthesis of N-alkyl derivatives (22 & 23)
General procedure: To a solution of 7-chloro-4-(piperazin-1-yl)quinoline (1mmol) in dry dichloroethane (6mL) was added the corresponding aldehyde (1.1mmol), freshly activated 3Å molecular sieves (0.25g) and catalytic amount of acetic acid. The reaction mixture was stirred at 30°C for 6h and filtered through celite bed (under N2 atmosphere). The solvent was removed under reduced pressure and residue further diluted with dry methanol (6mL) and cooled to 0°C. Sodium triacetoxy borohydride (1.5mmol) was added (portion-wise) and the reaction was stirred at 30°C for 6h (monitored by TLC & LCMS for completion for completion). The solvent was then removed under reduced pressure and the residue diluted with water (5mL) and extracted with dichloromethane (10mL). The aqueous phase was back-extracted with dichloromethane (2×10mL) and dried over sodium sulphate. The combined organic phases were concentrated under reduced and residue purified by column chromatography using hexane: ethylacetate as eluent to give the desired product in good yield. 4.1.7.1 4(4-((1H-Indol-3-yl)methyl)piperazin-1-yl)-7-chloroquinoline (22) The compound was synthesized according to the above general procedure using 7-chloro-4-(piperazin-1-yl)quinoline (0.25g, 1mmol), indole-2carboxaldehyde (0.16g, 1.1mmol), to afford 22 (0.23g, 60.5percent) as buff coloured solid. 1H NMR (DMSO-d6): δH. 2.59–2.64 (m, 2H), 3.12–3.19 (m, 4H), 3.56 (s, 2H), 7.06–8.63 (m, 10H), 9.78 (bs, 1H). 13C NMR
(DMSO-d6): δC. 155.9, 152.5, 149.6, 136.9, 133.4, 129.9, 128.6, 127.5, 125.7, 122.8, 122.3, 121.4, 119.3, 118.2, 111.9, 110.7, 109.8, 55.6, 51.8, 43.2. ESI-MS m/z 377.2 (M+H)+. Anal Calcd for C22H21ClN4; C, 70.11; H, 5.62; N, 14.87; Found C, 70.19; H, 5.67; N, 14.91.
115
Synthesize Find similar
Rx-ID: 40641137 Find similar reactions
13%
116
Synthesize Find similar
With sodium tris(acetoxy)borohydride in 1,2-dichloro-ethane
T=20°C; 24 h;
Synthesize Find similar
Rodrigues, Tiago; Hauser, Nadine; Reker, Daniel; Reutlinger, Michael; Wunderlin, Tiffany; Hamon, Jacques; Koch, Guido; Schneider, Gisbert
Angewandte Chemie - International Edition, 2015 , vol. 54, # 5 p. 1551 - 1555 Angew. Chem., 2015 , vol. 127, # 5 p. 1571 - 1575,5 Title/Abstract Full Text View citing articles Show Details
Synthesize Find similar
Rx-ID: 27873942 Find similar reactions
JANSSEN PHARMACEUTICA N.V.
Patent: WO2008/109333 A1, 2008 ; Location in patent: Page/Page column 55 ;
Title/Abstract Full Text Show Details
117
Synthesize Find similar
Rx-ID: 28548905 Find similar reactions
ASTRAZENECA AB; ASTRAZENECA UK LIMITED
Patent: WO2009/81197 A1, 2009 ; Location in patent: Page/Page column 196 ;
Title/Abstract Full Text Show Details
118
Synthesize Find similar
Rx-ID: 8742475 Find similar reactions
76%
With acetic acid in dichloromethane
T=20°C; Mannich reaction; 6 h;
Synthesize Find similar
Synthesize Find similar
Huebner; Kraxner; Gmeiner
Journal of Medicinal Chemistry, 2000 , vol. 43, # 23 p. 4563 - 4569 Title/Abstract Full Text View citing articles Show Details
Synthesize Find similar
119
Synthesize Find similar
Rx-ID: 40641136 Find similar reactions
Multi-step reaction with 2 steps 1: sodium cyanoborohydride; acetic acid / N,N-dimethyl acetamide / 0.17 h / 50 °C / |Flow reactor 2: water; acetonitrile / 0.27 h View Scheme
Synthesize Find similar
Synthesize Find similar
Rodrigues, Tiago; Hauser, Nadine; Reker, Daniel; Reutlinger, Michael; Wunderlin, Tiffany; Hamon, Jacques; Koch, Guido; Schneider, Gisbert
Angewandte Chemie - International Edition, 2015 , vol. 54, # 5 p. 1551 - 1555 Angew. Chem., 2015 , vol. 127, # 5 p. 1571 - 1575,5 Title/Abstract Full Text View citing articles Show Details
120
Synthesize Find similar
Rx-ID: 40641142 Find similar reactions
in water; acetonitrile
0.266667 h;
Synthesize Find similar
Synthesize Find similar
Rodrigues, Tiago; Hauser, Nadine; Reker, Daniel; Reutlinger, Michael; Wunderlin, Tiffany; Hamon, Jacques; Koch, Guido; Schneider, Gisbert
Angewandte Chemie - International Edition, 2015 , vol. 54, # 5 p. 1551 - 1555 Angew. Chem., 2015 , vol. 127, # 5 p. 1571 - 1575,5 Title/Abstract Full Text View citing articles Show Details
121
Synthesize Find similar
Rx-ID: 45401616 Find similar reactions
70%
in toluene
10 h; Reflux; Hide Experimental Procedure
Synthesize Find similar
Synthesize Find similar
Yin, Xiu-Juan; Huang, Xiao-Yan; Ma, Yun-Bao; Geng, Chang-An; Li, Tian-Ze; Chen, Xing-Long; Yang, Tong-Hua; Zhou, Jun; Zhang, Xue-Mei; Chen, Ji-Jun
Journal of Asian Natural Products Research, 2017 , vol. 19, # 6 p. 610 - 622
Title/Abstract Full Text View citing articles Show Details
4.2.4. General procedure for preparation of compound 19
The gramine (4 mmol) and 2-amino-ethyl-piperazine (2 mmol) were dissolved in dry toluene(15 ml). The mixture were refluxed for 10 h monitored by TLC. The solvent was removedin vacuo to afford crude products which were purified by column chromatography on silicagel using Et2NH /MeOH/CHCl3 (3:5: 92, v/v/v).N-[N-(3-Indolylmethyl)-aminoethyl]-N-piperazinyl-3-indolylmethylamine (19): Yellowoil, yield 70percent. 1H NMR (400 MHz, CDCl3) δH: 8.88 (s, 1H, NH), 8.85 (s, 1H, NH), 7.72-7.01(m, 10H, H-2, 2′, 4, 4′, 5, 5′, 6, 6′, 7, 7′), 3.98 (s, 2H, CH2 N), 3.72 (s, 2H, CH2CH2NHCH2),2.80–2.28 (m, 13H, 2-aminoethylpiperazinyl-H). 13C NMR (100 MHz, CDCl3) δ: 136.4(C-8, 8′), 128.1 (C-9), 127.0 (C-9′), 124.1 (C-2), 122.8 (C-2′), 122.0 (C-6), 121.8 (C-6′),119.4 (C-5), 119.4 (C-5′), 118.7 (C-4, 4′), 114.5 (C-3), 111.9 (C-3′), 111.3 (C-7), 111.1 (C-7′),57.4 (CH2 N), 53.1 (C3″, 5″), 53.0 (CH2 N), 52.7 (C-2″, 6″), 45.6 (CH2CH2NHCH2), 44.5(CH2CH2NHCH2). ESIMS: m/z 388 [M + H]+; HRESIMS: m/z 388.2477 [M + H]+ (calcdfor C24H29N5, 388.2496).
122
Synthesize Find similar
Rx-ID: 33537479 Find similar reactions
Synthesize Find similar
Synthesize Find similar
Synthesize Find similar
83%
in water
Mannich reaction; 2 h; Reflux;
Khan, Khalid Mohammed; Rahim, Fazal; Ambreen, Nida; Taha, Muhammad; Iqbal, Sarosh; Haider, Syed Moazzam; Perveen, Shahnaz
Journal of the Chemical Society of Pakistan, 2012 , vol. 34, # 3 p. 748 - 757 Title/Abstract Full Text View citing articles Show Details
in water
2 h; Reflux; Hide Experimental Procedure
Mesaik, M. Ahmed; Khan, Khalid Mohammed; Rahim, Fazal; Taha, Muhammad; Haider, Syed Moazzam; Perveen, Shahnaz; Khalid, Ahmed Shukralla; Abdalla, Omer M.; Soomro, Samreen; Voelter, Wolfgang
Bioorganic Chemistry, 2015 , vol. 60, p. 118 - 122 Title/Abstract Full Text View citing articles Show Details
5:
General procedure: Indole (3mmol), formaldehyde (1.2mmol), and secondary amine (3mmol), mL were mixed in reaction flask and then add distill water 10–15 and refluxed the solution for 2h with vigorous stirring. The reaction completion was checked by TLC, and the resulting solid mixture was then filter. In some cases solid mixture was not formed so it was extracted with ethyl acetate, purified by column chromatography using acetone and hexane system in 1:1 ratio, and pure product is obtained in 75–89percent yield [37].
123
Synthesize Find similar
Rx-ID: 23457135 Find similar reactions
OTSUKA PHARMACEUTICAL CO., LTD.
Patent: EP1555267 A1, 2005 ; Location in patent: Page/Page column 394 ; Title/Abstract Full Text Show Details
124
Synthesize Find similar
Rx-ID: 22949103 Find similar reactions
SUVEN LIFE SCIENCES LIMITED
Patent: WO2004/48330 A1, 2004 ; Location in patent: Page 52 ;
Title/Abstract Full Text Show Details
125
Synthesize Find similar
Rx-ID: 33537478 Find similar reactions
78%
in water
Mannich reaction; 2 h; Reflux;
Synthesize Find similar
Synthesize Find similar
Khan, Khalid Mohammed; Rahim, Fazal; Ambreen, Nida; Taha, Muhammad; Iqbal, Sarosh; Haider, Syed Moazzam; Perveen, Shahnaz
Journal of the Chemical Society of Pakistan, 2012 , vol. 34, # 3 p. 748 - 757 Title/Abstract Full Text View citing articles Show Details
126
Synthesize Find similar
Synthesize Find similar
Rx-ID: 28548921 Find similar reactions
ASTRAZENECA AB; ASTRAZENECA UK LIMITED
Patent: WO2009/81197 A1, 2009 ; Location in patent: Page/Page column 206 ; Title/Abstract Full Text Show Details
127
Synthesize Find similar
Rx-ID: 28549175 Find similar reactions
ASTRAZENECA AB; ASTRAZENECA UK LIMITED
Patent: WO2009/81197 A1, 2009 ; Location in patent: Page/Page column 133 ;
Title/Abstract Full Text Show Details
128
Synthesize Find similar
Rx-ID: 29685540 Find similar reactions
ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BRADBURY, Robert, Hugh; CARR, Gregory, Richard; RABOW, Alfred, Arthur; RAO KORUPOJU, Srinivasa; TUMMA, Harikrishna
Patent: WO2010/92371 A1, 2010 ; Location in patent: Page/Page column 102-103 ;
Title/Abstract Full Text Show Details
129
Synthesize Find similar
Rx-ID: 28548917 Find similar reactions
ASTRAZENECA AB; ASTRAZENECA UK LIMITED
Patent: WO2009/81197 A1, 2009 ; Location in patent: Page/Page column 206 ; Title/Abstract Full Text Show Details
130
Synthesize Find similar
Hide Experimental Procedure
Rx-ID: 25383100 Find similar reactions
Eisai Co., Ltd.
Patent: EP1254895 A1, 2002 ; Title/Abstract Full Text Show Details
5:Example 5
Example 5 1-[(4-Cyano-5-methyl-4-phenyl)hexyl]-4-[(3-indolyl)methyl]piperazine The title compound was obtained as a pale yellow oil in accordance with the method of Example 3 (76percent). Further, the hydrochloride of the title compound was obtained in a conventional method. Free body: 1H-NMR (400MHz, CDCl ) δ 0.76 (d, J = 6.8Hz, 3H), 1.04-1.18 (m, 1H), 1.18 (d, J = 6.8Hz, 3H), 1.47-1.60 (m, 1H), 1.86 (dt, J = 4.4Hz, J = 12.4Hz, 1H), 2.03-2.16 (m, 2H), 2.22-2.32 (m, 2H), 2.33 (bs, 4H), 2.49 (bs, 4H), 3
3.70 (s, 2H), 7.05-7.20 (m, 4H), 7.23-7.48 (m, 5H), 7.70 (d, J = 6.8Hz, 1H), 8.25-8.40 (m, 1H). Hydrochloride: ESI-Mass; 415 (MH+)
131
Synthesize Find similar
Rx-ID: 28548918 Find similar reactions
ASTRAZENECA AB; ASTRAZENECA UK LIMITED
Patent: WO2009/81197 A1, 2009 ; Location in patent: Page/Page column 206 ;
Title/Abstract Full Text Show Details
132
Synthesize Find similar
Rx-ID: 28548915 Find similar reactions
ASTRAZENECA AB; ASTRAZENECA UK LIMITED
Patent: WO2009/81197 A1, 2009 ; Location in patent: Page/Page column 205 ;
Title/Abstract Full Text Show Details
133
Synthesize Find similar
Hide Experimental Procedure
Rx-ID: 23882886 Find similar reactions
Li, Qun; Woods, Keith W.; Zhu, Gui-Dong; Fischer, John P.; Gong, Jianchun; Li, Tongmei; Gandhi, Virajkumar; Thomas, Sheela A.; Packard, Garrick K.; Song, Xiaohong; Abrams, Jason N.; Diebold, Robert B.; Dinges, Jurgen; Hutchins, Charles W.; Stoll, Vincent S.; Rosenberg, Saul H.; Giranda, Vincent L.
Patent: US2003/199511 A1, 2003 ; Location in patent: Page/Page column 44 ; Title/Abstract Full Text Show Details
130:6-(5-(4-(1H-Indol-3-ylmethyl)-piperazin-1-yl)-pyridin-3-yl)-isoquinoline
EXAMPLE 130 6-(5-(4-(1H-Indol-3-ylmethyl)-piperazin-1-yl)-pyridin-3-yl)-isoquinoline The title compound was prepared by substituting Example 124 for aniline, and 3-formylindole for Example 116A in example 116B. MS (ESI) (m/z 420M+H)+; 1H NMR (400 MHz, DMSO-D6) δ ppm 1.89 (s, 2H) 2.50 (m, 4H) 2.60 (m, 4H) 7.02 (m, 2H) 7.27 (d, J=2.46 Hz, 1H) 7.36 (d, J=7.98 Hz, 1H) 7.68 (m, 2H) 7.87 (d, J=5.83 Hz, 1H) 8.05 (dd, J=8.59, 1.53 Hz, 1H) 8.22 (d, J=8.90 Hz, 1H) 8.34 (m, 2H) 8.44 (d, J=1.84 Hz, 1H) 8.54 (d, J=5.83 Hz, 1H) 9.35 (s, 1H) 10.93 (s, 1H).
134
Synthesize Find similar
Hide Experimental Procedure
Synthesize Find similar
Rx-ID: 23928857 Find similar reactions
Li, Qun; Woods, Keith W.; Zhu, Gui-Dong; Fischer, John P.; Gong, Jianchun; Li, Tongmei; Gandhi, Virajkumar; Thomas, Sheela A.; Packard, Garrick K.; Song, Xiaohong; Abrams, Jason N.; Diebold, Robert; Dinges, Jurgen; Hutchins, Charles; Stoll, Vincent S.; Rosenberg, Saul H.; Giranda, Vincent L.
Patent: US2003/187026 A1, 2003 ; Title/Abstract Full Text Show Details
130:6-(5-(4-(1H-Indol-3-ylmethyl)-piperazin-1-yl)-pyridin-3-yl)-isoquinoline
EXAMPLE 130 6-(5-(4-(1H-Indol-3-ylmethyl)-piperazin-1-yl)-pyridin-3-yl)-isoquinoline The title compound was prepared by substituting Example 124 for aniline, and 3-formylindole for Example 116A in example 116B. MS (ESI) (m/z 420M+H)+; 1H NMR (400 MHz, DMSO-D6) δ ppm 1.89 (s, 2H) 2.50 (m, 4H) 2.60 (m, 4H) 7.02 (m, 2H) 7.27 (d, J=2.46 Hz, 1H) 7.36 (d, J=7.98 Hz, 1H) 7.68 (m, 2H) 7.87 (d, J=5.83 Hz, 1H) 8.05 (dd, J=8.59, 1.53 Hz, 1H) 8.22 (d, J=8.90 Hz, 1H) 8.34 (m, 2H) 8.44 (d, J=1.84 Hz, 1H) 8.54 (d, J=5.83 Hz, 1H) 9.35 (s, 1H) 10.93 (s, 1H).
135
Synthesize Find similar
Rx-ID: 29685541 Find similar reactions
ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BRADBURY, Robert, Hugh; CARR, Gregory, Richard; RABOW, Alfred, Arthur; RAO KORUPOJU, Srinivasa; TUMMA, Harikrishna
Patent: WO2010/92371 A1, 2010 ; Location in patent: Page/Page column 102-103 ;
Title/Abstract Full Text Show Details
136
Synthesize Find similar
Rx-ID: 5954000 Find similar reactions
Amin 7, /BRN= 403117/, NEt3;
Glamkowski et al.
Journal of Medicinal Chemistry, 1977 , vol. 20, p. 1485 Full Text View citing articles Show Details
Entspr. NH-Verb., Acyl.;
Hoechst
Patent: FR2272673DE2522143 , 1975 ; Chem.Abstr., vol. 84, # 90183 Full Text Show Details
137
Synthesize Find similar
Rx-ID: 28548909 Find similar reactions
ASTRAZENECA AB; ASTRAZENECA UK LIMITED
Patent: WO2009/81197 A1, 2009 ; Location in patent: Page/Page column 204 ;
Title/Abstract Full Text Show Details
138
Synthesize Find similar
Rx-ID: 29685542 Find similar reactions
ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BRADBURY, Robert, Hugh; CARR, Gregory, Richard; RABOW, Alfred, Arthur; RAO KORUPOJU, Srinivasa; TUMMA, Harikrishna
Patent: WO2010/92371 A1, 2010 ; Location in patent: Page/Page column 102-103 ;
Title/Abstract Full Text Show Details
139
Synthesize Find similar
Rx-ID: 46083498 Find similar reactions
85%
Synthesize Find similar
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine in N,N-dimethylformamide
T=20°C; 4 h; Hide Experimental Procedure
Synthesize Find similar
Phoenix Molecular Designs; DUNN, Sandra E.; JAYANTHAN, Aarthi; NAGIREDDY, Jaipal Reddy; ANNEDI, Subhash; VAN DRIE, John H.; DAYNARD, Timothy S.; HUYNH, My-my
Patent: US2017/240549 A1, 2017 ; Location in patent: Paragraph 0665; 0667 ; Title/Abstract Full Text Show Details
3.B:
B. A solution of 3-((4-methylpiperazin-1-yl)methyl)-1H-indol-5-amine (compound 3b, 0.175 g, 0.716 mmol), 1-benzyl-1H-pyrazole-4-carboxylic acid (compound 1c, 0.16 g, 0.787 mmol) and Et3N (0.2 mL, 1.432 mmol) in dry DMF (5 mL) was treated with HBTU (0.27 g, 0.716 mmol) at room temperature and stirred for 4 h. The reaction was diluted with 1N NaOH solution (50 mL), water (50 mL) and product was extracted into ethyl acetate (2*50 mL). The combined ethyl acetate layer was washed with brine (50 mL) and dried (Na2SO4). Solvent was evaporated and crude was purified by column chromatography (2M NH3 in MeOH:CH2Cl2, 2:98 to 5:95) on silica gel to obtain 1-benzyl-N-(3-((4-methylpiperazin-1-yl)methyl)-1H-indol-5-yl)-1H-pyrazole-4carboxamide, compound No.3, (0.26 g, 85percent) as a pale yellow solid. 1H NMR (DMSO-d6) δ 2.21 (s, 3H), 2.25-2.40 (m, 8H), 3.55 (s, 2H), 5.39 (s, 2H), 7.19 (d, 1H, J=1.2 Hz), 7.27-7.39 (m, 7H), 7.83 (s, 1H), 8.06 (s, 1H), 8.41 (s, 1H), 9.69 (s, 1H), 10.85 (s, 1H); ESI-MS (m/z, percent): 429 (MH+, 100percent).
140
Synthesize Find similar
Synthesize Find similar
Multi-step reaction with 2 steps 1: hydrazine hydrate / methanol / 20 °C / Reflux 2: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 4 h / 20 °C View Scheme
Rx-ID: 46083508 Find similar reactions
Phoenix Molecular Designs; DUNN, Sandra E.; JAYANTHAN, Aarthi; NAGIREDDY, Jaipal Reddy; ANNEDI, Subhash; VAN DRIE, John H.; DAYNARD, Timothy S.; HUYNH, My-my
Patent: US2017/240549 A1, 2017 ; Title/Abstract Full Text Show Details
141
Synthesize Find similar
Rx-ID: 28548911 Find similar reactions
ASTRAZENECA AB; ASTRAZENECA UK LIMITED
Patent: WO2009/81197 A1, 2009 ; Location in patent: Page/Page column 204 ;
Title/Abstract Full Text Show Details
142
Synthesize Find similar
Rx-ID: 10786688 Find similar reactions
SCHERING CORPORATION
Patent: WO2007/126964 A2, 2007 ; Location in patent: Page/Page column 100 ; Title/Abstract Full Text Show Details
143
Synthesize Find similar
Rx-ID: 9180861 Find similar reactions
70%
Synthesize Find similar
With sodium tris(acetoxy)borohydride in 1,2-dichloro-ethane
Synthesize Find similar
Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.
Australian Journal of Chemistry, 2002 , vol. 55, # 9 p. 565 - 576 Title/Abstract Full Text View citing articles Show Details
144
Synthesize Find similar
Multi-step reaction with 5 steps 1: 74 percent / K2CO3; Cu / various solvent(s) / 4 h / Heating 2: 64 percent / Na2S2O4 / aq. NH3 / 80 °C 3: 79 percent / xylene / 96 h / Heating 4: 69 percent / TiCl4 / dioxane / 24 h / Heating 5: 70 percent / NaBH(OAc)3 / 1,2-dichloro-ethane View Scheme
Synthesize Find similar
Rx-ID: 14560971 Find similar reactions
Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.
Australian Journal of Chemistry, 2002 , vol. 55, # 9 p. 565 - 576 Title/Abstract Full Text View citing articles Show Details
145
Synthesize Find similar
Multi-step reaction with 3 steps 1: 79 percent / xylene / 96 h / Heating 2: 69 percent / TiCl4 / dioxane / 24 h / Heating 3: 70 percent / NaBH(OAc)3 / 1,2-dichloro-ethane View Scheme
Synthesize Find similar
Rx-ID: 14562106 Find similar reactions
Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.
Australian Journal of Chemistry, 2002 , vol. 55, # 9 p. 565 - 576 Title/Abstract Full Text View citing articles Show Details
146
Synthesize Find similar
Multi-step reaction with 4 steps 1: 64 percent / Na2S2O4 / aq. NH3 / 80 °C 2: 79 percent / xylene / 96 h / Heating 3: 69 percent / TiCl4 / dioxane / 24 h / Heating 4: 70 percent / NaBH(OAc)3 / 1,2-dichloro-ethane View Scheme
Synthesize Find similar
Rx-ID: 14562162 Find similar reactions
Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.
Australian Journal of Chemistry, 2002 , vol. 55, # 9 p. 565 - 576 Title/Abstract Full Text View citing articles Show Details
147
Synthesize Find similar
Multi-step reaction with 5 steps 1: 74 percent / K2CO3; Cu / various solvent(s) / 4 h / Heating 2: 64 percent / Na2S2O4 / aq. NH3 / 80 °C 3: 79 percent / xylene / 96 h / Heating 4: 69 percent / TiCl4 / dioxane / 24 h / Heating 5: 70 percent / NaBH(OAc)3 / 1,2-dichloro-ethane View Scheme
Synthesize Find similar
Rx-ID: 14567978 Find similar reactions
Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.
Australian Journal of Chemistry, 2002 , vol. 55, # 9 p. 565 - 576 Title/Abstract Full Text View citing articles Show Details
148
Synthesize Find similar
Multi-step reaction with 2 steps 1: 69 percent / TiCl4 / dioxane / 24 h / Heating 2: 70 percent / NaBH(OAc)3 / 1,2-dichloro-ethane View Scheme
Synthesize Find similar
Rx-ID: 14578296 Find similar reactions
Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.
Australian Journal of Chemistry, 2002 , vol. 55, # 9 p. 565 - 576 Title/Abstract Full Text View citing articles Show Details
149
Synthesize Find similar
Multi-step reaction with 3 steps 1.1: dichloromethane / 1 h / Inert atmosphere 1.2: 48 h / 20 °C / Inert atmosphere 2.1: hydrogen bromide / water / 12 h / 125 °C / Inert atmosphere 3.1: dichloromethane / 1 h / Inert atmosphere 3.2: 48 h / 20 °C / Inert atmosphere View Scheme
Synthesize Find similar
Rx-ID: 33504036 Find similar reactions
Johnson, Mark; Antonio, Tamara; Reith, Maarten E. A.; Dutta, Aloke K.
Journal of Medicinal Chemistry, 2012 , vol. 55, # 12 p. 5826 - 5840 Title/Abstract Full Text View citing articles Show Details
150
Synthesize Find similar
Rx-ID: 33504061 Find similar reactions
77%
Stage #1: in dichloromethane
1 h; Inert atmosphere; Stage #2: With sodium tris(acetoxy)borohydride in dichloromethane
T=20°C; 48 h; Inert atmosphere;
Synthesize Find similar
Synthesize Find similar
Johnson, Mark; Antonio, Tamara; Reith, Maarten E. A.; Dutta, Aloke K.
Journal of Medicinal Chemistry, 2012 , vol. 55, # 12 p. 5826 - 5840 Title/Abstract Full Text View citing articles Show Details
151
Synthesize Find similar
Multi-step reaction with 2 steps
Synthesize Find similar
Rx-ID: 33504232 Find similar reactions
Johnson, Mark; Antonio, Tamara; Reith, Maarten E. A.; Dutta, Aloke K.
1.1: hydrogen bromide / water / 12 h / 125 °C / Inert atmosphere 2.1: dichloromethane / 1 h / Inert atmosphere 2.2: 48 h / 20 °C / Inert atmosphere View Scheme
Journal of Medicinal Chemistry, 2012 , vol. 55, # 12 p. 5826 - 5840 Title/Abstract Full Text View citing articles Show Details
152
Synthesize Find similar
Multi-step reaction with 4 steps 1.1: acetic acid / dichloromethane / 0.5 h / Inert atmosphere 1.2: 0 - 20 °C / Inert atmosphere 2.1: dichloromethane / 1 h / Inert atmosphere 2.2: 48 h / 20 °C / Inert atmosphere 3.1: hydrogen bromide / water / 12 h / 125 °C / Inert atmosphere 4.1: dichloromethane / 1 h / Inert atmosphere 4.2: 48 h / 20 °C / Inert atmosphere View Scheme
Synthesize Find similar
Rx-ID: 33504236 Find similar reactions
Johnson, Mark; Antonio, Tamara; Reith, Maarten E. A.; Dutta, Aloke K.
Journal of Medicinal Chemistry, 2012 , vol. 55, # 12 p. 5826 - 5840 Title/Abstract Full Text View citing articles Show Details
153
Synthesize Find similar
154
Multi-step reaction with 3 steps 1.1: dichloromethane / 1 h / Inert atmosphere 1.2: 48 h / 20 °C / Inert atmosphere 2.1: hydrogen bromide / water / 12 h / 125 °C / Inert atmosphere 3.1: dichloromethane / 1 h / Inert atmosphere 3.2: 48 h / 20 °C / Inert atmosphere View Scheme
Synthesize Find similar
Rx-ID: 33504243 Find similar reactions
Johnson, Mark; Antonio, Tamara; Reith, Maarten E. A.; Dutta, Aloke K.
Journal of Medicinal Chemistry, 2012 , vol. 55, # 12 p. 5826 - 5840 Title/Abstract Full Text View citing articles Show Details
Synthesize Find similar
Multi-step reaction with 4 steps 1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 1.2: 1.5 h / -78 - 20 °C / Inert atmosphere 2.1: dichloromethane / 1 h / Inert atmosphere 2.2: 48 h / 20 °C / Inert atmosphere 3.1: hydrogen bromide / water / 12 h / 125 °C / Inert atmosphere 4.1: dichloromethane / 1 h / Inert atmosphere 4.2: 48 h / 20 °C / Inert atmosphere View Scheme
Synthesize Find similar
Rx-ID: 33504272 Find similar reactions
Johnson, Mark; Antonio, Tamara; Reith, Maarten E. A.; Dutta, Aloke K.
Journal of Medicinal Chemistry, 2012 , vol. 55, # 12 p. 5826 - 5840 Title/Abstract Full Text View citing articles Show Details
155
Synthesize Find similar
77%
With boron tribromide in dichloromethane
T=20°C; 5 h;
Synthesize Find similar
Rx-ID: 9228343 Find similar reactions
Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.
Australian Journal of Chemistry, 2002 , vol. 55, # 9 p. 565 - 576 Title/Abstract Full Text View citing articles Show Details
156
Synthesize Find similar
Multi-step reaction with 6 steps 1: 74 percent / K2CO3; Cu / various solvent(s) / 4 h / Heating 2: 64 percent / Na2S2O4 / aq. NH3 / 80 °C 3: 79 percent / xylene / 96 h / Heating 4: 69 percent / TiCl / dioxane / 24 h / Heating
Synthesize Find similar
Rx-ID: 14560976 Find similar reactions
Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.
Australian Journal of Chemistry, 2002 , vol. 55, # 9 p. 565 - 576 Title/Abstract Full Text View citing articles Show Details
4
5: 79 percent / NaBH(OAc)3 / 1,2-dichloro-ethane 6: 77 percent / BBr3 / CH2Cl2 / 5 h / 20 °C View Scheme
157
Synthesize Find similar
Multi-step reaction with 4 steps 1: 79 percent / xylene / 96 h / Heating 2: 69 percent / TiCl4 / dioxane / 24 h / Heating 3: 79 percent / NaBH(OAc)3 / 1,2-dichloro-ethane 4: 77 percent / BBr3 / CH2Cl2 / 5 h / 20 °C View Scheme
Synthesize Find similar
Rx-ID: 14562111 Find similar reactions
Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.
Australian Journal of Chemistry, 2002 , vol. 55, # 9 p. 565 - 576 Title/Abstract Full Text View citing articles Show Details
158
Synthesize Find similar
Multi-step reaction with 5 steps 1: 64 percent / Na2S2O4 / aq. NH3 / 80 °C 2: 79 percent / xylene / 96 h / Heating 3: 69 percent / TiCl4 / dioxane / 24 h / Heating 4: 79 percent / NaBH(OAc)3 / 1,2-dichloro-ethane 5: 77 percent / BBr3 / CH2Cl2 / 5 h / 20 °C View Scheme
Synthesize Find similar
Rx-ID: 14562167 Find similar reactions
Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.
Australian Journal of Chemistry, 2002 , vol. 55, # 9 p. 565 - 576 Title/Abstract Full Text View citing articles Show Details
159
Synthesize Find similar
Synthesize Find similar
Rx-ID: 14567983 Find similar reactions
Multi-step reaction with 6 steps 1: 74 percent / K2CO3; Cu / various solvent(s) / 4 h / Heating 2: 64 percent / Na2S2O4 / aq. NH3 / 80 °C 3: 79 percent / xylene / 96 h / Heating 4: 69 percent / TiCl4 / dioxane / 24 h / Heating 5: 79 percent / NaBH(OAc)3 / 1,2-dichloro-ethane 6: 77 percent / BBr3 / CH2Cl2 / 5 h / 20 °C View Scheme
Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.
Australian Journal of Chemistry, 2002 , vol. 55, # 9 p. 565 - 576 Title/Abstract Full Text View citing articles Show Details
160
Synthesize Find similar
Multi-step reaction with 2 steps 1: 79 percent / NaBH(OAc)3 / 1,2-dichloro-ethane 2: 77 percent / BBr3 / CH2Cl2 / 5 h / 20 °C View Scheme
Synthesize Find similar
Rx-ID: 14573664 Find similar reactions
Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.
Australian Journal of Chemistry, 2002 , vol. 55, # 9 p. 565 - 576 Title/Abstract Full Text View citing articles Show Details
161
Synthesize Find similar
162
Multi-step reaction with 3 steps 1: 69 percent / TiCl4 / dioxane / 24 h / Heating 2: 79 percent / NaBH(OAc)3 / 1,2-dichloro-ethane 3: 77 percent / BBr3 / CH2Cl2 / 5 h / 20 °C View Scheme
Synthesize Find similar
Rx-ID: 14578298 Find similar reactions
Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.
Australian Journal of Chemistry, 2002 , vol. 55, # 9 p. 565 - 576 Title/Abstract Full Text View citing articles Show Details
Synthesize Find similar
Rx-ID: 28548919 Find similar reactions
ASTRAZENECA AB; ASTRAZENECA UK LIMITED
Patent: WO2009/81197 A1, 2009 ; Location in patent: Page/Page column 206 ;
Title/Abstract Full Text Show Details
163
Synthesize Find similar
Rx-ID: 2755098 Find similar reactions
85%
With sodium hydrogencarbonate in tetrahydrofuran; N,Ndimethyl-formamide
5 h; Heating;
Synthesize Find similar
Synthesize Find similar
Malleron, Jean-Luc; Gueremy, Claude; Mignani, Serge; Peyronel, Jean-Francois; Truchon, Alain; et al.
Journal of Medicinal Chemistry, 1993 , vol. 36, # 9 p. 1194 - 1202 Title/Abstract Full Text View citing articles Show Details
164
Synthesize Find similar
Synthesize Find similar
Rx-ID: 31808257 Find similar reactions
Multi-step reaction with 3 steps 1: trichlorophosphate 2: sodium tris(acetoxy)borohydride; acetic acid / dichloromethane 3: lithium perchlorate / acetonitrile / Reflux View Scheme
Na, Young Min
Bulletin of the Korean Chemical Society, 2011 , vol. 32, # 1 p. 307 - 310 Title/Abstract Full Text View citing articles Show Details
Multi-step reaction with 2 steps 1: trichlorophosphate 2: sodium tris(acetoxy)borohydride; acetic acid / dichloromethane View Scheme
Na, Young Min
Bulletin of the Korean Chemical Society, 2011 , vol. 32, # 1 p. 307 - 310 Title/Abstract Full Text View citing articles Show Details
165
Synthesize Find similar
Multi-step reaction with 2 steps 1: sodium tris(acetoxy)borohydride; acetic acid / dichloromethane 2: lithium perchlorate / acetonitrile / Reflux View Scheme
Synthesize Find similar
Rx-ID: 31808322 Find similar reactions
Na, Young Min
Bulletin of the Korean Chemical Society, 2011 , vol. 32, # 1 p. 307 - 310 Title/Abstract Full Text View citing articles Show Details
166
Synthesize Find similar
Rx-ID: 31808325 Find similar reactions
With sodium tris(acetoxy)borohydride; acetic acid in dichloromethane
Synthesize Find similar
Synthesize Find similar
Na, Young Min
Bulletin of the Korean Chemical Society, 2011 , vol. 32, # 1 p. 307 - 310 Title/Abstract Full Text View citing articles Show Details
167
Synthesize Find similar
Synthesize Find similar
Rx-ID: 31808543 Find similar reactions
Multi-step reaction with 2 steps 1: lithium perchlorate / acetonitrile / Reflux 2: sodium tris(acetoxy)borohydride; acetic acid / dichloromethane View Scheme
Na, Young Min
Bulletin of the Korean Chemical Society, 2011 , vol. 32, # 1 p. 307 - 310 Title/Abstract Full Text View citing articles Show Details
Multi-step reaction with 2 steps
Na, Young Min
1.1: lithium perchlorate / acetonitrile / 48 h / Reflux 2.1: acetic acid / ethanol / 1 h / 0 °C 2.2: 12 h / 0 - 40 °C View Scheme
Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details
168
Synthesize Find similar
Rx-ID: 31808546 Find similar reactions
Synthesize Find similar
With lithium perchlorate in acetonitrile
Reflux;
Synthesize Find similar
Na, Young Min
Bulletin of the Korean Chemical Society, 2011 , vol. 32, # 1 p. 307 - 310 Title/Abstract Full Text View citing articles Show Details
169
Synthesize Find similar
Rx-ID: 32943556 Find similar reactions
Synthesize Find similar
Stage #1: formaldehyd; (2R,3R)-2-(2,4-difluorophenyl)-3(piperazin-1-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol With acetic acid in ethanol
T=0°C; 1 h; Stage #2: indole in ethanol
T=0 - 40°C; 12 h;
Synthesize Find similar
Na, Young Min
Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details
170
Synthesize Find similar
Synthesize Find similar
Rx-ID: 32943580 Find similar reactions
Synthesize Find similar
Multi-step reaction with 7 steps 1.1: dichloromethane / 70 °C 2.1: potassium carbonate / 6 h / 100 °C 3.1: toluene-4-sulfonic acid / methanol / 1 h / 20 °C 4.1: pyridine / 6 h / 20 °C 5.1: sodium methylate / methanol / 0.5 h / 0 °C 6.1: lithium perchlorate / acetonitrile / 48 h / Reflux 7.1: acetic acid / ethanol / 1 h / 0 °C 7.2: 12 h / 0 - 40 °C View Scheme
Na, Young Min
Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details
171
Synthesize Find similar
Multi-step reaction with 4 steps 1.1: pyridine / 6 h / 20 °C 2.1: sodium methylate / methanol / 0.5 h / 0 °C 3.1: lithium perchlorate / acetonitrile / 48 h / Reflux 4.1: acetic acid / ethanol / 1 h / 0 °C 4.2: 12 h / 0 - 40 °C View Scheme
Synthesize Find similar
Rx-ID: 32943626 Find similar reactions
Na, Young Min
Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details
172
Synthesize Find similar
173
Multi-step reaction with 3 steps 1.1: sodium methylate / methanol / 0.5 h / 0 °C 2.1: lithium perchlorate / acetonitrile / 48 h / Reflux 3.1: acetic acid / ethanol / 1 h / 0 °C 3.2: 12 h / 0 - 40 °C View Scheme
Synthesize Find similar
Rx-ID: 32943650 Find similar reactions
Na, Young Min
Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details
Synthesize Find similar
Synthesize Find similar
Multi-step reaction with 5 steps 1.1: toluene-4-sulfonic acid / methanol / 1 h / 20 °C 2.1: pyridine / 6 h / 20 °C 3.1: sodium methylate / methanol / 0.5 h / 0 °C 4.1: lithium perchlorate / acetonitrile / 48 h / Reflux 5.1: acetic acid / ethanol / 1 h / 0 °C 5.2: 12 h / 0 - 40 °C View Scheme
Rx-ID: 32943676 Find similar reactions
Na, Young Min
Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details
174
Synthesize Find similar
Synthesize Find similar
Multi-step reaction with 6 steps 1.1: potassium carbonate / 6 h / 100 °C 2.1: toluene-4-sulfonic acid / methanol / 1 h / 20 °C 3.1: pyridine / 6 h / 20 °C 4.1: sodium methylate / methanol / 0.5 h / 0 °C 5.1: lithium perchlorate / acetonitrile / 48 h / Reflux 6.1: acetic acid / ethanol / 1 h / 0 °C 6.2: 12 h / 0 - 40 °C View Scheme
Rx-ID: 32943701 Find similar reactions
Na, Young Min
Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details
175
Synthesize Find similar
With methanol; sodium cyanoborohydride
T=20°C; 40 h;
Rx-ID: 45192906 Find similar reactions
EXONATE LIMITED; BATES, David; MORRIS, Jonathan; TOOP, Hamish; BATSON, Jennifer
Patent: WO2017/64512 A1, 2017 ;
Location in patent: Page/Page column 34; 55 ;
Hide Experimental Procedure
Title/Abstract Full Text Show Details
General Procedure for the Syntheses of Compound 4
General procedure: Piperazine 3 (1 equiv.) and sodium cyanoborohydride (2 equiv.) were added successively as solids to a 0.1M solution of the R3 aldehyde (R3 as defined elsewhere) (1 equiv.) in methanol. The solution was allowed to stir at room temperature for 40 h. The solvent was removed under reduced pressure. The residue was diluted with saturated aqueous sodium bicarbonate solution and extracted with dichloromethane (x3). The organic extracts were combined and washed with brine, then dried (Na2SO4). The solvent was removed under reduced pressure. The crude product was purified by flash chromatography on deactivated silica gel, eluting with 2 - 5 percent methanol/ethyl acetate, to afford the product.
176
Synthesize Find similar
Rx-ID: 25623754 Find similar reactions
SCHERING CORPORATION
Patent: WO2007/11623 A1, 2007 ; Location in patent: Page/Page column 316 ;
Title/Abstract Full Text Show Details
177
Synthesize Find similar
Rx-ID: 9183117 Find similar reactions
79%
Synthesize Find similar
With sodium tris(acetoxy)borohydride in 1,2-dichloro-ethane
Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.
Australian Journal of Chemistry, 2002 , vol. 55, # 9 p. 565 - 576 Title/Abstract Full Text View citing articles Show Details
178
Synthesize
Synthesize Find similar
Synthesize
Find similar
Multi-step reaction with 5 steps 1: 74 percent / K2CO3; Cu / various solvent(s) / 4 h / Heating 2: 64 percent / Na2S2O4 / aq. NH3 / 80 °C 3: 79 percent / xylene / 96 h / Heating 4: 69 percent / TiCl4 / dioxane / 24 h / Heating 5: 79 percent / NaBH(OAc)3 / 1,2-dichloro-ethane View Scheme
Find similar
Rx-ID: 14560975 Find similar reactions
Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.
Australian Journal of Chemistry, 2002 , vol. 55, # 9 p. 565 - 576 Title/Abstract Full Text View citing articles Show Details
179
Synthesize Find similar
Multi-step reaction with 3 steps 1: 79 percent / xylene / 96 h / Heating 2: 69 percent / TiCl4 / dioxane / 24 h / Heating 3: 79 percent / NaBH(OAc)3 / 1,2-dichloro-ethane View Scheme
Synthesize Find similar
Rx-ID: 14562110 Find similar reactions
Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.
Australian Journal of Chemistry, 2002 , vol. 55, # 9 p. 565 - 576 Title/Abstract Full Text View citing articles Show Details
180
Synthesize Find similar
181
Multi-step reaction with 4 steps 1: 64 percent / Na2S2O4 / aq. NH3 / 80 °C 2: 79 percent / xylene / 96 h / Heating 3: 69 percent / TiCl4 / dioxane / 24 h / Heating 4: 79 percent / NaBH(OAc)3 / 1,2-dichloro-ethane View Scheme
Synthesize Find similar
Rx-ID: 14562166 Find similar reactions
Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.
Australian Journal of Chemistry, 2002 , vol. 55, # 9 p. 565 - 576 Title/Abstract Full Text View citing articles Show Details
Synthesize Find similar
Synthesize Find similar
Multi-step reaction with 5 steps 1: 74 percent / K2CO3; Cu / various solvent(s) / 4 h / Heating 2: 64 percent / Na2S2O4 / aq. NH3 / 80 °C 3: 79 percent / xylene / 96 h / Heating 4: 69 percent / TiCl4 / dioxane / 24 h / Heating 5: 79 percent / NaBH(OAc)3 / 1,2-dichloro-ethane View Scheme
Rx-ID: 14567982 Find similar reactions
Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.
Australian Journal of Chemistry, 2002 , vol. 55, # 9 p. 565 - 576 Title/Abstract Full Text View citing articles Show Details
182
Synthesize Find similar
Synthesize Find similar
Multi-step reaction with 2 steps 1: 69 percent / TiCl4 / dioxane / 24 h / Heating 2: 79 percent / NaBH(OAc)3 / 1,2-dichloro-ethane View Scheme
Rx-ID: 14578297 Find similar reactions
Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.
Australian Journal of Chemistry, 2002 , vol. 55, # 9 p. 565 - 576 Title/Abstract Full Text View citing articles Show Details
183
Synthesize Find similar
Rx-ID: 23339493 Find similar reactions
KUDOS PHARMACEUTICALS LIMITED; MAYBRIDGE LIMITED
Patent: WO2004/80976 A1, 2004 ; Location in patent: Page 87 ; Title/Abstract Full Text Show Details
184
Synthesize Find similar
With methanol; sodium cyanoborohydride
T=20°C; 40 h; Hide Experimental Procedure
Rx-ID: 45192870 Find similar reactions
EXONATE LIMITED; BATES, David; MORRIS, Jonathan; TOOP, Hamish; BATSON, Jennifer
Patent: WO2017/64512 A1, 2017 ; Location in patent: Page/Page column 34; 47 ; Title/Abstract Full Text Show Details
General Procedure for the Syntheses of Compound 4
General procedure: Piperazine 3 (1 equiv.) and sodium cyanoborohydride (2 equiv.) were added successively as solids to a 0.1M solution of the R3 aldehyde (R3 as defined elsewhere) (1 equiv.) in methanol. The solution was allowed to stir at room temperature for 40 h. The solvent was removed under reduced pressure. The residue was diluted with saturated aqueous sodium bicarbonate solution and extracted with dichloromethane (x3). The organic extracts were combined and washed with brine, then dried (Na2SO4). The solvent was removed under reduced pressure. The crude product was purified by flash chromatography on deactivated silica gel, eluting with 2 - 5 percent methanol/ethyl acetate, to afford the product.
185
Synthesize Find similar
Rx-ID: 28548913 Find similar reactions
ASTRAZENECA AB; ASTRAZENECA UK LIMITED
Patent: WO2009/81197 A1, 2009 ; Location in patent: Page/Page column 204 ;
Title/Abstract Full Text Show Details
186
Synthesize Find similar
Rx-ID: 32943574 Find similar reactions
Synthesize Find similar
Synthesize Find similar
Synthesize Find similar
Stage #1: formaldehyd; (2R,3R)-2-(2,4-difluorophenyl)-3(piperazin-1-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol With acetic acid in ethanol
T=0°C; 1 h; Stage #2: 5-methyl-1H-indole in ethanol
T=0 - 40°C; 12 h;
Na, Young Min
Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details
187
Synthesize Find similar
Multi-step reaction with 7 steps 1.1: dichloromethane / 70 °C 2.1: potassium carbonate / 6 h / 100 °C 3.1: toluene-4-sulfonic acid / methanol / 1 h / 20 °C 4.1: pyridine / 6 h / 20 °C 5.1: sodium methylate / methanol / 0.5 h / 0 °C 6.1: lithium perchlorate / acetonitrile / 48 h / Reflux 7.1: acetic acid / ethanol / 1 h / 0 °C 7.2: 12 h / 0 - 40 °C View Scheme
Synthesize Find similar
Rx-ID: 32943586 Find similar reactions
Na, Young Min
Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details
188
Synthesize Find similar
189
Multi-step reaction with 2 steps 1.1: lithium perchlorate / acetonitrile / 48 h / Reflux 2.1: acetic acid / ethanol / 1 h / 0 °C 2.2: 12 h / 0 - 40 °C View Scheme
Synthesize Find similar
Rx-ID: 32943608 Find similar reactions
Na, Young Min
Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details
Synthesize Find similar
Multi-step reaction with 4 steps 1.1: pyridine / 6 h / 20 °C 2.1: sodium methylate / methanol / 0.5 h / 0 °C 3.1: lithium perchlorate / acetonitrile / 48 h / Reflux 4.1: acetic acid / ethanol / 1 h / 0 °C 4.2: 12 h / 0 - 40 °C View Scheme
Synthesize Find similar
Rx-ID: 32943632 Find similar reactions
Na, Young Min
Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details
190
Synthesize Find similar
Multi-step reaction with 3 steps 1.1: sodium methylate / methanol / 0.5 h / 0 °C 2.1: lithium perchlorate / acetonitrile / 48 h / Reflux 3.1: acetic acid / ethanol / 1 h / 0 °C 3.2: 12 h / 0 - 40 °C View Scheme
Synthesize Find similar
Rx-ID: 32943656 Find similar reactions
Na, Young Min
Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details
191
Synthesize Find similar
192
Multi-step reaction with 5 steps 1.1: toluene-4-sulfonic acid / methanol / 1 h / 20 °C 2.1: pyridine / 6 h / 20 °C 3.1: sodium methylate / methanol / 0.5 h / 0 °C 4.1: lithium perchlorate / acetonitrile / 48 h / Reflux 5.1: acetic acid / ethanol / 1 h / 0 °C 5.2: 12 h / 0 - 40 °C View Scheme
Synthesize Find similar
Rx-ID: 32943682 Find similar reactions
Na, Young Min
Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details
Synthesize Find similar
Synthesize Find similar
Multi-step reaction with 6 steps 1.1: potassium carbonate / 6 h / 100 °C 2.1: toluene-4-sulfonic acid / methanol / 1 h / 20 °C 3.1: pyridine / 6 h / 20 °C 4.1: sodium methylate / methanol / 0.5 h / 0 °C 5.1: lithium perchlorate / acetonitrile / 48 h / Reflux 6.1: acetic acid / ethanol / 1 h / 0 °C 6.2: 12 h / 0 - 40 °C View Scheme
Rx-ID: 32943707 Find similar reactions
Na, Young Min
Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details
193
Synthesize Find similar
Rx-ID: 32943561 Find similar reactions
72%
Synthesize Find similar
Stage #1: formaldehyd; (2R,3R)-2-(2,4-difluorophenyl)-3(piperazin-1-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol With acetic acid in ethanol
T=0°C; 1 h; Stage #2: 5-fluoro-1H-indole in ethanol
T=0 - 40°C; 12 h;
Synthesize Find similar
Na, Young Min
Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details
194
Synthesize Find similar
Multi-step reaction with 7 steps 1.1: dichloromethane / 70 °C
Synthesize Find similar
Rx-ID: 32943583 Find similar reactions
Na, Young Min
Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470
Synthesize Find similar
2.1: potassium carbonate / 6 h / 100 °C 3.1: toluene-4-sulfonic acid / methanol / 1 h / 20 °C 4.1: pyridine / 6 h / 20 °C 5.1: sodium methylate / methanol / 0.5 h / 0 °C 6.1: lithium perchlorate / acetonitrile / 48 h / Reflux 7.1: acetic acid / ethanol / 1 h / 0 °C 7.2: 12 h / 0 - 40 °C View Scheme
Title/Abstract Full Text View citing articles Show Details
195
Synthesize Find similar
Multi-step reaction with 2 steps 1.1: lithium perchlorate / acetonitrile / 48 h / Reflux 2.1: acetic acid / ethanol / 1 h / 0 °C 2.2: 12 h / 0 - 40 °C View Scheme
Synthesize Find similar
Rx-ID: 32943605 Find similar reactions
Na, Young Min
Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details
196
Synthesize Find similar
197
Multi-step reaction with 4 steps 1.1: pyridine / 6 h / 20 °C 2.1: sodium methylate / methanol / 0.5 h / 0 °C 3.1: lithium perchlorate / acetonitrile / 48 h / Reflux 4.1: acetic acid / ethanol / 1 h / 0 °C 4.2: 12 h / 0 - 40 °C View Scheme
Synthesize Find similar
Rx-ID: 32943629 Find similar reactions
Na, Young Min
Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details
Synthesize Find similar Multi-step reaction with 3 steps 1.1: sodium methylate / methanol / 0.5 h / 0 °C 2.1: lithium perchlorate / acetonitrile / 48 h / Reflux 3.1: acetic acid / ethanol / 1 h / 0 °C 3.2: 12 h / 0 - 40 °C View Scheme
Synthesize Find similar
Rx-ID: 32943653 Find similar reactions
Na, Young Min
Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details
198
Synthesize Find similar Multi-step reaction with 5 steps 1.1: toluene-4-sulfonic acid / methanol / 1 h / 20 °C 2.1: pyridine / 6 h / 20 °C 3.1: sodium methylate / methanol / 0.5 h / 0 °C 4.1: lithium perchlorate / acetonitrile / 48 h / Reflux 5.1: acetic acid / ethanol / 1 h / 0 °C 5.2: 12 h / 0 - 40 °C View Scheme
Synthesize Find similar
Rx-ID: 32943679 Find similar reactions
Na, Young Min
Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 11 p. 3467 - 3470 Title/Abstract Full Text View citing articles Show Details