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17 reactions in Reaxys
2017-11-10 23h:31m:34s (EST)
GH N
N
1. Query GH
NH
Search as: As drawn, No mixtures, No isotopes, No charges, No radicals
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H N
H N
NH
N H
Cl
N
NH
Rx-ID: 36697875 View in Reaxys 1/17 Yield
Conditions & References With potassium carbonate in N,N-dimethyl-formamide, Time= 16h, T= 120 °C Aristotelous, Tonia; Ahn, Seungkirl; Shukla, Arun K.; Gawron, Sylwia; Sassano, Maria F.; Kahsai, Alem W.; Wingler, Laura M.; Zhu, Xiao; Tripathi-Shukla, Prachi; Huang, Xi-Ping; Riley, Jennifer; Besnard, Jeremy; Read, Kevin D.; Roth, Bryan L.; Gilbert, Ian H.; Hopkins, Andrew L.; Lefkowitz, Robert J.; Navratilova, Iva; ACS Medicinal Chemistry Letters; vol. 4; nb. 10; (2013); p. 1005 - 1010 View in Reaxys
N
N
HN
Rx-ID: 23459118 View in Reaxys 2/17 Yield
Conditions & References
60 %
19 Patent; ELI LILLY AND COMPANY; WO2005/66126; (2005); (A1) English View in Reaxys
N N N
N
N
HN
O
Rx-ID: 30095106 View in Reaxys 3/17 Yield
Conditions & References 5-Bromo-3-(4-methylpiperazin-1-yl)-1H-indole (6h) General procedure: Intermediate obtained as above was stirred with 85 percent potassium hydroxide (0.0038 mmole) in ethanol at reflux temperature. The progress of the reaction was monitored by TLC. After completion of the reaction, solvent was removed under pressure. The residual mass was dissolved in 100 mL ethyl acetate and the separated organic layer was washed with brine solution and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residual mass was purified by flash chromatography over silica gel using ethyl acetate containing 1 percent triethylamine as eluent to obtain the intermediate 5-Bromo-3-(4-methylpiperazin-1-yl)-1H-indole in 90 percent yield. With potassium hydroxide in ethanol, Reflux Nirogi, Ramakrishna V.S.; Deshpande, Amol D.; Kambhampati, Ramasastri; Badange, Rajesh Kumar; Kota, Laxman; Daulatabad, Anand V.; Shinde, Anil K.; Ahmad, Ishtiyaque; Kandikere, Vishwottam; Jayarajan, Pradeep; Dubey; Bioorganic and Medicinal Chemistry Letters; vol. 21; nb. 1; (2011); p. 346 - 349 View in Reaxys
Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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N
N
N
N
N
NH
O
Rx-ID: 30095107 View in Reaxys 4/17 Yield
Conditions & References 5-Bromo-3-(4-methylpiperazin-1-yl)-1H-indole (6h) General procedure: Intermediate obtained as above was stirred with 85 percent potassium hydroxide (0.0038 mmole) in ethanol at reflux temperature. The progress of the reaction was monitored by TLC. After completion of the reaction, solvent was removed under pressure. The residual mass was dissolved in 100 mL ethyl acetate and the separated organic layer was washed with brine solution and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residual mass was purified by flash chromatography over silica gel using ethyl acetate containing 1 percent triethylamine as eluent to obtain the intermediate 5-Bromo-3-(4-methylpiperazin-1-yl)-1H-indole in 90 percent yield. With potassium hydroxide in ethanol, Reflux Nirogi, Ramakrishna V.S.; Deshpande, Amol D.; Kambhampati, Ramasastri; Badange, Rajesh Kumar; Kota, Laxman; Daulatabad, Anand V.; Shinde, Anil K.; Ahmad, Ishtiyaque; Kandikere, Vishwottam; Jayarajan, Pradeep; Dubey; Bioorganic and Medicinal Chemistry Letters; vol. 21; nb. 1; (2011); p. 346 - 349 View in Reaxys
NH Cl N
N
Rx-ID: 6095509 View in Reaxys 5/17 Yield
Conditions & References resp. N-Acetylindol, NaOH Patent; Lab. Sauba S.A.; DE2811031; (1978); ; vol. 90; nb. 38962 View in Reaxys
N
N
N Cl
N Cl
N
NH
O
Rx-ID: 30095109 View in Reaxys 6/17 Yield
Conditions & References 5-Bromo-3-(4-methylpiperazin-1-yl)-1H-indole (6h) General procedure: Intermediate obtained as above was stirred with 85 percent potassium hydroxide (0.0038 mmole) in ethanol at reflux temperature. The progress of the reaction was monitored by TLC. After completion of the reaction, solvent was removed under pressure. The residual mass was dissolved in 100 mL ethyl acetate and the separated organic layer was washed with brine solution and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residual mass was purified by flash chromatography over silica gel using ethyl acetate containing 1 percent triethylamine as eluent to obtain the intermediate 5-Bromo-3-(4-methylpiperazin-1-yl)-1H-indole in 90 percent yield. With potassium hydroxide in ethanol, Reflux
Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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Nirogi, Ramakrishna V.S.; Deshpande, Amol D.; Kambhampati, Ramasastri; Badange, Rajesh Kumar; Kota, Laxman; Daulatabad, Anand V.; Shinde, Anil K.; Ahmad, Ishtiyaque; Kandikere, Vishwottam; Jayarajan, Pradeep; Dubey; Bioorganic and Medicinal Chemistry Letters; vol. 21; nb. 1; (2011); p. 346 - 349 View in Reaxys
N
N
N
N
Br
Br N
NH
O
Rx-ID: 30095108 View in Reaxys 7/17 Yield
Conditions & References
90 %
5-Bromo-3-(4-methylpiperazin-1-yl)-1H-indole (6h) General procedure: Intermediate obtained as above was stirred with 85 percent potassium hydroxide (0.0038 mmole) in ethanol at reflux temperature. The progress of the reaction was monitored by TLC. After completion of the reaction, solvent was removed under pressure. The residual mass was dissolved in 100 mL ethyl acetate and the separated organic layer was washed with brine solution and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residual mass was purified by flash chromatography over silica gel using ethyl acetate containing 1 percent triethylamine as eluent to obtain the intermediate 5-Bromo-3-(4-methylpiperazin-1-yl)-1H-indole in 90 percent yield. With potassium hydroxide in ethanol, Reflux Nirogi, Ramakrishna V.S.; Deshpande, Amol D.; Kambhampati, Ramasastri; Badange, Rajesh Kumar; Kota, Laxman; Daulatabad, Anand V.; Shinde, Anil K.; Ahmad, Ishtiyaque; Kandikere, Vishwottam; Jayarajan, Pradeep; Dubey; Bioorganic and Medicinal Chemistry Letters; vol. 21; nb. 1; (2011); p. 346 - 349 View in Reaxys
O
O
O O
N
N
N
N
N
NH
O
Rx-ID: 25916961 View in Reaxys 8/17 Yield 89 %
Conditions & References 5 :Into a 250 mL round bottom flask was placed a solution of tert-butyl 4-(l-acetyl-lH-indol- 3-yl) piperazine-1 -carboxylate (2.6 g, 7.58 mmol) in methanol (80 mL). To the mixture was added Et3N (2.3 g, 22.73 mmol). The resulting solution was allowed to react, with stirring, for 1 hour while the temperature was maintained at reflux in a bath of oil. The reaction progress was monitored by LCMS and TLC (ethyl acetate/petroleum, ether = 1:1). The mixture was concentrated by evaporation under vacuum using a rotary evaporator. The resulting solution was diluted with 200 mL of ethyl acetate. The resulting mixture was washed 3 times with 150 mL of NaCl(aq.). The residue was purified by eluting through a column with a 10:1 petroleum ether/ethyl acetate solvent system. This resulted in 2.1 g (89percent) of tert-butyl 4-(lH-indol-3-yl) piperazine-1 -carboxylate as a light pink solid.1H NMR (400MHz, CDCl3) δ 1.55 (9H, s), 3.1 (4H, s), 3.7 (4H, s), 6.7 (IH, s), 7.21 (IH, t), 7.32 (IH, t), 7.34 (IH, d), 7.68 (IH, d), 7.7 (IH, d). m/z 302 (M++].). With triethylamine in methanol, Time= 1h, Heating / reflux Patent; MEMORY PHARMACEUTICALS CORPORATION; WO2007/98418; (2007); (A1) English View in Reaxys
Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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N
Br N Br
N
N NH
N O
Rx-ID: 10698892 View in Reaxys 9/17 Yield
Conditions & References
51 %
2 :Description 2: 3-(4-Ethylpiperazin-l-yl)-5-bromo indole:; N-Acetyl-3-(4-ethyIpiperazin-l-yI)-5-bromoindole (4.6 g) technical material obtained as above was stirred with methanolic solution of 85 percent potassium hydroxide (2.55 g, 3.87 mM in 46 mL of methanol) at reflux temperature. The progress of reaction was monitored by TLC. After completion of reaction, solvent was removed under vacuum. The residual mass was dissolved in 100 mL ethyl acetate. The organic layer was washed with brine solution and dried over anhydrous magnesium sulfate. Solvent removal under vacuum yielded the desired product (3.7 g, 91 percent yield). Column purification from silica gel, 100 - 200 mesh size using ethyl acetate containing 1 percent triethyl amine as eluent afforded the pure product in 51 percent yield. Mass (m/z): 308.2, 310.2 (M+H)+; 1H-NMR (δ ppm): 1.13 - 1.16 (3H, t, J = 7.20), 2.49 - 2.55 (2H, q, J = 7.24), 2.69 (4H, bs), 3.11 (4H, bs), 6.753 - 6.759 (IH, d, J = 2.44), 7.17 - 7.19 (IH, d, J = 8.6), 7.24 - 7.26 (IH, dd, J = 8.68, 2.0), 7.73 (IH, bs), 7.75 - 7.76 (IH, d, J = 1.6). With methanol, potassium hydroxide, Heating / reflux Patent; SUVEN LIFE SCIENCES LIMITED; WO2007/138611; (2007); (A1) English View in Reaxys 5-Bromo-3-(4-methylpiperazin-1-yl)-1H-indole (6h) General procedure: Intermediate obtained as above was stirred with 85 percent potassium hydroxide (0.0038 mmole) in ethanol at reflux temperature. The progress of the reaction was monitored by TLC. After completion of the reaction, solvent was removed under pressure. The residual mass was dissolved in 100 mL ethyl acetate and the separated organic layer was washed with brine solution and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residual mass was purified by flash chromatography over silica gel using ethyl acetate containing 1 percent triethylamine as eluent to obtain the intermediate 5-Bromo-3-(4-methylpiperazin-1-yl)-1H-indole in 90 percent yield. With potassium hydroxide in ethanol, Reflux Nirogi, Ramakrishna V.S.; Deshpande, Amol D.; Kambhampati, Ramasastri; Badange, Rajesh Kumar; Kota, Laxman; Daulatabad, Anand V.; Shinde, Anil K.; Ahmad, Ishtiyaque; Kandikere, Vishwottam; Jayarajan, Pradeep; Dubey; Bioorganic and Medicinal Chemistry Letters; vol. 21; nb. 1; (2011); p. 346 - 349 View in Reaxys
NH Cl N N
Rx-ID: 6113895 View in Reaxys 10/17 Yield
Conditions & References resp. N-Acetylindol, NaOH Patent; Lab. Sauba S.A.; DE2811031; (1978); ; vol. 90; nb. 38962 View in Reaxys
Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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NH
N N
O
O
Rx-ID: 6134798 View in Reaxys 11/17 Yield
Conditions & References Chlorhydrat B-2, NaOH Patent; Lab. Sauba S.A.; DE2811031; (1978); ; vol. 90; nb. 38962 View in Reaxys
NH
N N F F F
Rx-ID: 6137648 View in Reaxys 12/17 Yield
Conditions & References N-Acetylindol B-1, NaOH Patent; Lab. Sauba S.A.; DE2811031; (1978); ; vol. 90; nb. 38962 View in Reaxys F
O
N
N NH
NH
O
Rx-ID: 22993166 View in Reaxys 13/17 Yield
Conditions & References 95 Patent; GLAXO GROUP LIMITED; WO2004/46124; (2004); (A1) English View in Reaxys
O
NH N N
N
NH O N
Rx-ID: 25350474 View in Reaxys 14/17 Yield
Conditions & References Particularly preferred compounds of the present invention represented by formula (I) include: ... 2-[4-(5-trifluoromethylpyridin-2-yl)piperazin-1-yl]-6-pyridin-4-ylpyrimidin-4(1H)-one, 2-[4-(quinolin-2-yl)piperazin-1-yl]-6-pyridin-4-ylpyrimidin-4(1H)-one, 2-[4-(imidazo[1,2-a ]pyridin-5-yl)piperazin-1-yl]-6-pyridin-4-ylpyrimidin-4(1H)-one, 2-[4-(1H -indazol-4-yl)piperazin-1-yl]-6-pyridin-4-ylpyrimidin-4(1H)-one, 2-[4-(5-methoxy-1H -indol-3-yl)piperazin-1-yl]-6-pyridin-4-ylpyrimidin-4(1H)-one,
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2-[4-(imidazo[4,5-c ]pyridin-4-yl)piperazin-1-yl]-6-pyridin-4-ylpyrimidin-4(1H)-one, 2-[4-(1H -indazol-7-yl)piperazin-1-yl)-6-pyridin-4-ylpyrimidin-4(1H)-one, 2-[4-(4-methoxy-1H -benzimidazol-7-yl)piperazin-1-yl]-6-pyridin-4-ylpyrimidin-4(1H)-one, ... Patent; SANOFI-SYNTHELABO; Mitsubishi-Tokyo Pharmaceuticals, Inc.; EP1136483; (2001); (A1) English View in Reaxys A pyrimidone derivative which is selected from the group consisting of: ... 2-[4-(5-trifluoromethylpyridin-2-yl)piperazin-1-yl]-6-pyridin-4-ylpyrimidin-4(1H)-one, 2-[4-(quinolin-2-yl)piperazin-1-yl]-6-pyridin-4-ylpyrimidin-4(1H)-one, 2-[4-(imidazo[1,2-a ]pyridin-5-yl)piperazin-1-yl]-6-pyridin-4-ylpyrimidin-4(1H)-one, 2-[4-(1H -indazol-4-yl)piperazin-1-yl]-6-pyridin-4-ylpyrimidin-4(1H)-one, 2-[4-(5-methoxy-1H -indol-3-yl)piperazin-1-yl]-6-pyridin-4-ylpyrimidin-4(1H)-one, 2-[4-(imidazo[4,5-c ]pyridin-4-yl)piperazin-1-yl]-6-pyridin-4-ylpyrimidin-4(1H)-one, 2-[4-(1H -indazol-7-yl)piperazin-1-yl]-6-pyridin-4-ylpyrimidin-4(1H)-one, 2-[4-(4-methoxy-1H -benzimidazol-7-yl)piperazin-1-yl]-6-pyridin-4-ylpyrimidin-4(1H)-one, ... Patent; SANOFI-SYNTHELABO; Mitsubishi-Tokyo Pharmaceuticals, Inc.; EP1136483; (2001); (A1) English View in Reaxys Cl
O
O
N
N NH
NH
Rx-ID: 22993167 View in Reaxys 15/17 Yield
Conditions & References 96 Patent; GLAXO GROUP LIMITED; WO2004/46124; (2004); (A1) English View in Reaxys
O HN
N
O
S
O
N
N O HN
Rx-ID: 45146041 View in Reaxys 16/17 Yield
Conditions & References 3.5 : Step 7) 3- (1 - ((4-methoxy-3- (piperazin-1-yl) phenyl) sulfonyl) piperidin-4-yl) lH-indole bondedto General procedure: A solution of 1- (4- (5 - ((4- (1H-indol-3-yl) piperidin-1-yl) sulfonyl) -2-methoxyphenyl)piperazine1-yl) -2,2,2-trifluoroethanone (900 mg, 1.63 mmol) was dissolved ina mixed solvent of tetrahydrofuran(10 mL), ethanol (10 mL) and water(10 mL) followed by potassium carbonate (662 mg, 4.8 Mmol).After the reaction was stirred for 24 hours,dichloromethane (60 mL) was added, washed with saturated sodium chloride solution (30 mL), and the organic phase was separated and dried over anhydrous sodium sulfate.Filtered,the filtrate by rotary evaporation under reduced pressure, purified by column chromatography (dichloromethane / methanol (v / v) = 20/ 1)to give the title compound as a white solid(690mg, 93percent). With potassium carbonate in tetrahydrofuran, ethanol, water, Time= 24h, T= 25 °C Patent; Guangdong East Sunshine Pharmaceutical Co., Ltd; Jin, Chunfei; Zhong, Wenhe; Zhang, Yingjun; (40 pag.); CN106045966; (2016); (A) Chinese
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View in Reaxys
O
NH O
NH N
N N
Rx-ID: 31601601 View in Reaxys 17/17 Yield
Conditions & References 112 Patent; Dainippon Sumitomo Pharma Co., Ltd.; MARUYAMA, Megumi; KINOMURA, Naoya; NOJIMA, Satoshi; TAKAMURA, Masahiro; KAKIGUCHI, Keisuke; TATAMITANI, Hiroto; WO2011/111875; (2011); (A1) English View in Reaxys
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