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Date
N O
1. Query
465 reactions in 2016-02-23 21h:59m:44s (EST) Reaxys
O
NH N
Search as: Substructure: on all atoms, No salts, No mixtures 2. Query
(1. Query) AND itemno in (1,5,6,7,8,9,16,15,10)
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9 reactions in Reaxys
2016-02-23 22h:10m:40s (EST)
2016-02-23 22:12:08
H N O N
HN H 2N
O
Yield
Conditions & References
N
Rx-ID: 25675369 View in Reaxys 1/9 50 %
N,N-Dimethyl-(2,3,4,9-tetrahydro-1H-carbazole-3-yl)amine (13a). General procedure: Aqueous sulfuric acid solution (10 percent w/v, 30 mL) was taken in a round bottom flask, added (1,4-dioxa-spiro[4.5]dec-8-yl)dimethylamine (12a, 1.5 g, 8.1 mmol) followed by phenylhydrazine (1.52 g, 14.08 mmol) at room temperature. The reaction mass was heated to reflux temperature (95-100 °C) and maintained reflux for 2-3 h. The progress of the reaction was monitored by TLC. After completion of reaction, the reaction mass was cooled to 10-15 °C. Then the mass was basified with aqueous sodium hydroxide solution (20 percent w/v) and the aqueous layer was extracted with ethyl acetate. Organic layer was washed with brine solution, dried over anhydrous sodium sulfate and organic volatiles were removed by distillation under vacuum. The crude compound was purified by flash chromatography (ethyl acetate: triethylamine 9:0.2) to obtain 0.8 g of title compound (13a), the yield being 50 percent. HPLC (percent): 98.10, mp (°C): 132.8-139.1; IR (cm-1): 3143, 3054, 2921, 2828, 2729, 1623, 1585, 741; ESI-MS (m/z): 215.1 (M+H)+; 1H-NMR (400 MHz, CDCl3): d 1.80-1.85 (m, 1H, C2-H), 2.20-2.23 (m, 1H, C2-H), 2.45 (s, 6H, N-(CH3)2), 2.64-2.67 (m, 1H, C4-H), 2.77-2.85 (m, 3H, C1, C3-H), 2.95-3.00 (m, 1H, C4-H), 7.07-7.15 (m, 2H, C6, C7-H), 7.27-7.29 (d, 1H, J = 8.02 Hz, C5-H) 7.46-7.48 (d, 1H, J = 7.4 Hz, C8-H), 7.88 (bs, 1H, NH). With sulfuric acid in water, T= 95 - 100 °C Nirogi, Ramakrishna V. S.; Konda, Jagadishu Babu; Kambhampati, Ramasastry; Shinde, Anil; Bandyala, Thrinath Reddy; Gudla, Parandhama; Kandukuri, Kiran Kumar; Jayarajan, Pradeep; Kandikere, Vishwottam; Dubey, P. K.; Bioorganic and Medicinal Chemistry Letters; vol. 22; nb. 22; (2012); p. 6980 - 6985,6 View in Reaxys Aqueous sulphuric acid (10percent w/v) solution 30 ml was taken in a round bottom flask, added 4-N,N-Dimethylamino cyclohexanone ethylene ketal (1.5 gm, 8.1 mM) followed by Phenyl hydrazine (1.52 gm, 14.08 mM) at room temperature. Then the reaction mass was heated to reflux temperature (95-100° C.) and maintained reflux for 2-3 hours. The progress of the reaction was monitored by TLC. After completion of reaction, the reaction mass was cooled to RT and then to 10-15° C. Then the mass was basified with aq. NaOH solution (20percent w/v) and the aqueous layer was extracted with ethylacetate. Layers separated. Organic phase was washed with brine solution, dried over anhydrous sodium sulfate and removed solvent by distillation under vacuum. The residual mass was purified by flash chromatography (Ethylacetate:Triethylamine is 9:0.2). Stage 1: With sulfuric acid in water, T= 20 - 100 °C Stage 2: With sodium hydroxide in water Patent; Ramakrishna, Venkata Satya Nirogi; Kambhampati, Rama Sastri; Shirsath, Vikas Shreekrishna; US2010/189646; (2010); (A1) English View in Reaxys 2 :Intermediate 2; DimethyI-(2,3,4,9-tetrahydro-lH-carbazole -3-yl)amine; Procedure: Aqueous sulphuric acid (10percent w/v) solution 30ml was taken in a round bottom flask, added 4- N, N-Dimethylamino cyclohexanone ethylene ketal (1.5 gm, 8.1 mM) followed by Phenyl hydrazine (1.52 gm, 14.08 mM) at room temperature. Then the reaction mass was heated to reflux temperature (95-100 0C) and maintained reflux for 2-3 hours. The progress of the reaction was monitored by TLC. After completion of reaction, the reaction mass was cooled to RT and then to 10-15 0C. Then the mass was basified with aq. NaOH solution ( 20percent w/v ) EPO <DP n="18"/>and the aqueous layer was extracted with ethylacetate. Layers separated. Organic phase was washed with brine solution, dried over anhydrous sodium sulfate and removed solvent by distillation under vaccum. The residual mass was purified by flash chromatography (Ethylacetate : Triethylamine is 9:0.2). IR spectra (an 1): 3141, 3054, 2921, 2831, 2729, 1626, 1591, 743; Melting range (0C): 132.8 - 139.1; Mass (m/z): 214.9 (M+H)+; 1H-NMR (δ, ppm): 1.80 - 1.91 (IH, m), 2.19 - 2.27 (IH, m), 2.42 (6H, s), 2.64 - 2.67 (lH,m), 2.78 - 2.83 (3H3 m), 2.93 - 2.97 (IH, m), 7.05 - 7.13 (2H, m), 7.25 - 7.26 (IH, m) 7.45 - 7.46 (IH, db, m), 7.90 (IH, bs). With sulfuric acid in water, Time= 2 - 3h, T= 25 - 100 °C Patent; SUVEN LIFE SCIENCES INC.; WO2007/46111; (2007); (A1) English View in Reaxys
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Br N
O
HN
Br
N O
H 2N
N H
Rx-ID: 34209199 View in Reaxys 2/9 Yield
Conditions & References #10;N,N-Dimethyl-(2,3,4,9-tetrahydro-1H-carbazole-3-yl)amine (13a). #10;#10; General procedure: Aqueous sulfuric acid solution (10 percent w/v, 30 mL) was taken in a round bottom flask, added (1,4-dioxa-spiro[4.5]dec-8-yl)dimethylamine (12a, 1.5 g, 8.1 mmol) followed by phenylhydrazine (1.52 g, 14.08 mmol) at room temperature. The reaction mass was heated to reflux temperature (95-100 °C) and maintained reflux for 2-3 h. The progress of the reaction was monitored by TLC. After completion of reaction, the reaction mass was cooled to 10-15 °C. Then the mass was basified with aqueous sodium hydroxide solution (20 percent w/v) and the aqueous layer was extracted with ethyl acetate. Organic layer was washed with brine solution, dried over anhydrous sodium sulfate and organic volatiles were removed by distillation under vacuum. The crude compound was purified by flash chromatography (ethyl acetate: triethylamine 9:0.2) to obtain 0.8 g of title compound (13a), the yield being 50 percent. With sulfuric acid in water, T= 95 - 100 °C Nirogi, Ramakrishna V. S.; Konda, Jagadishu Babu; Kambhampati, Ramasastry; Shinde, Anil; Bandyala, Thrinath Reddy; Gudla, Parandhama; Kandukuri, Kiran Kumar; Jayarajan, Pradeep; Kandikere, Vishwottam; Dubey, P. K.; Bioorganic and Medicinal Chemistry Letters; vol. 22; nb. 22; (2012); p. 6980 - 6985,6 View in Reaxys
N
O
HN
Cl
Cl
N O
H 2N
N H
Rx-ID: 34209200 View in Reaxys 3/9 Yield
Conditions & References #10;N,N-Dimethyl-(2,3,4,9-tetrahydro-1H-carbazole-3-yl)amine (13a). #10;#10; General procedure: Aqueous sulfuric acid solution (10 percent w/v, 30 mL) was taken in a round bottom flask, added (1,4-dioxa-spiro[4.5]dec-8-yl)dimethylamine (12a, 1.5 g, 8.1 mmol) followed by phenylhydrazine (1.52 g, 14.08 mmol) at room temperature. The reaction mass was heated to reflux temperature (95-100 °C) and maintained reflux for 2-3 h. The progress of the reaction was monitored by TLC. After completion of reaction, the reaction mass was cooled to 10-15 °C. Then the mass was basified with aqueous sodium hydroxide solution (20 percent w/v) and the aqueous layer was extracted with ethyl acetate. Organic layer was washed with brine solution, dried over anhydrous sodium sulfate and organic volatiles were removed by distillation under vacuum. The crude compound was purified by flash chromatography (ethyl acetate: triethylamine 9:0.2) to obtain 0.8 g of title compound (13a), the yield being 50 percent. #10;#10; With sulfuric acid in water, T= 95 - 100 °C Nirogi, Ramakrishna V. S.; Konda, Jagadishu Babu; Kambhampati, Ramasastry; Shinde, Anil; Bandyala, Thrinath Reddy; Gudla, Parandhama; Kandukuri, Kiran Kumar; Jayarajan, Pradeep; Kandikere, Vishwottam; Dubey, P. K.; Bioorganic and Medicinal Chemistry Letters; vol. 22; nb. 22; (2012); p. 6980 - 6985,6 View in Reaxys
H N O
HN H 2N
F
N O
N
F
Rx-ID: 34209201 View in Reaxys 4/9 Yield
Conditions & References #10;N,N-Dimethyl-(2,3,4,9-tetrahydro-1H-carbazole-3-yl)amine (13a). #10;#10; General procedure: Aqueous sulfuric acid solution (10 percent w/v, 30 mL) was taken in a round bottom flask, added (1,4-dioxa-spiro[4.5]dec-8-yl)dimethylamine (12a, 1.5 g, 8.1 mmol) followed by phenylhydrazine (1.52 g, 14.08 mmol) at room temperature. The reaction mass was heated to reflux temperature (95-100 °C) and maintained reflux for 2-3 h. The progress of the reaction was monitored by TLC. After completion of reaction, the reaction mass was cooled to 10-15 °C. Then the mass was basified with aqueous sodium hydroxide solution (20 percent w/v) and the aqueous layer
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was extracted with ethyl acetate. Organic layer was washed with brine solution, dried over anhydrous sodium sulfate and organic volatiles were removed by distillation under vacuum. The crude compound was purified by flash chromatography (ethyl acetate: triethylamine 9:0.2) to obtain 0.8 g of title compound (13a), the yield being 50 percent. #10;#10; With sulfuric acid in water, T= 95 - 100 °C Nirogi, Ramakrishna V. S.; Konda, Jagadishu Babu; Kambhampati, Ramasastry; Shinde, Anil; Bandyala, Thrinath Reddy; Gudla, Parandhama; Kandukuri, Kiran Kumar; Jayarajan, Pradeep; Kandikere, Vishwottam; Dubey, P. K.; Bioorganic and Medicinal Chemistry Letters; vol. 22; nb. 22; (2012); p. 6980 - 6985,6 View in Reaxys
H N O O
NH NH 2
N O
N
O
Rx-ID: 34209202 View in Reaxys 5/9 Yield
Conditions & References #10;N,N-Dimethyl-(2,3,4,9-tetrahydro-1H-carbazole-3-yl)amine (13a). #10;#10; General procedure: Aqueous sulfuric acid solution (10 percent w/v, 30 mL) was taken in a round bottom flask, added (1,4-dioxa-spiro[4.5]dec-8-yl)dimethylamine (12a, 1.5 g, 8.1 mmol) followed by phenylhydrazine (1.52 g, 14.08 mmol) at room temperature. The reaction mass was heated to reflux temperature (95-100 °C) and maintained reflux for 2-3 h. The progress of the reaction was monitored by TLC. After completion of reaction, the reaction mass was cooled to 10-15 °C. Then the mass was basified with aqueous sodium hydroxide solution (20 percent w/v) and the aqueous layer was extracted with ethyl acetate. Organic layer was washed with brine solution, dried over anhydrous sodium sulfate and organic volatiles were removed by distillation under vacuum. The crude compound was purified by flash chromatography (ethyl acetate: triethylamine 9:0.2) to obtain 0.8 g of title compound (13a), the yield being 50 percent. #10;#10; With sulfuric acid in water, T= 95 - 100 °C Nirogi, Ramakrishna V. S.; Konda, Jagadishu Babu; Kambhampati, Ramasastry; Shinde, Anil; Bandyala, Thrinath Reddy; Gudla, Parandhama; Kandukuri, Kiran Kumar; Jayarajan, Pradeep; Kandikere, Vishwottam; Dubey, P. K.; Bioorganic and Medicinal Chemistry Letters; vol. 22; nb. 22; (2012); p. 6980 - 6985,6 View in Reaxys
N S
O S
NH NH 2
N O
N H
Rx-ID: 34209203 View in Reaxys 6/9 Yield
Conditions & References #10;N,N-Dimethyl-(2,3,4,9-tetrahydro-1H-carbazole-3-yl)amine (13a). #10;#10; General procedure: Aqueous sulfuric acid solution (10 percent w/v, 30 mL) was taken in a round bottom flask, added (1,4-dioxa-spiro[4.5]dec-8-yl)dimethylamine (12a, 1.5 g, 8.1 mmol) followed by phenylhydrazine (1.52 g, 14.08 mmol) at room temperature. The reaction mass was heated to reflux temperature (95-100 °C) and maintained reflux for 2-3 h. The progress of the reaction was monitored by TLC. After completion of reaction, the reaction mass was cooled to 10-15 °C. Then the mass was basified with aqueous sodium hydroxide solution (20 percent w/v) and the aqueous layer was extracted with ethyl acetate. Organic layer was washed with brine solution, dried over anhydrous sodium sulfate and organic volatiles were removed by distillation under vacuum. The crude compound was purified by flash chromatography (ethyl acetate: triethylamine 9:0.2) to obtain 0.8 g of title compound (13a), the yield being 50 percent. #10;#10; With sulfuric acid in water, T= 95 - 100 °C Nirogi, Ramakrishna V. S.; Konda, Jagadishu Babu; Kambhampati, Ramasastry; Shinde, Anil; Bandyala, Thrinath Reddy; Gudla, Parandhama; Kandukuri, Kiran Kumar; Jayarajan, Pradeep; Kandikere, Vishwottam; Dubey, P. K.; Bioorganic and Medicinal Chemistry Letters; vol. 22; nb. 22; (2012); p. 6980 - 6985,6 View in Reaxys
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F
H 2N HN
H N
O
F
N O
F
F
N
Rx-ID: 34209204 View in Reaxys 7/9 Yield
Conditions & References #10;N,N-Dimethyl-(2,3,4,9-tetrahydro-1H-carbazole-3-yl)amine (13a). #10;#10; General procedure: Aqueous sulfuric acid solution (10 percent w/v, 30 mL) was taken in a round bottom flask, added (1,4-dioxa-spiro[4.5]dec-8-yl)dimethylamine (12a, 1.5 g, 8.1 mmol) followed by phenylhydrazine (1.52 g, 14.08 mmol) at room temperature. The reaction mass was heated to reflux temperature (95-100 °C) and maintained reflux for 2-3 h. The progress of the reaction was monitored by TLC. After completion of reaction, the reaction mass was cooled to 10-15 °C. Then the mass was basified with aqueous sodium hydroxide solution (20 percent w/v) and the aqueous layer was extracted with ethyl acetate. Organic layer was washed with brine solution, dried over anhydrous sodium sulfate and organic volatiles were removed by distillation under vacuum. The crude compound was purified by flash chromatography (ethyl acetate: triethylamine 9:0.2) to obtain 0.8 g of title compound (13a), the yield being 50 percent. #10;#10; With sulfuric acid in water, T= 95 - 100 °C Nirogi, Ramakrishna V. S.; Konda, Jagadishu Babu; Kambhampati, Ramasastry; Shinde, Anil; Bandyala, Thrinath Reddy; Gudla, Parandhama; Kandukuri, Kiran Kumar; Jayarajan, Pradeep; Kandikere, Vishwottam; Dubey, P. K.; Bioorganic and Medicinal Chemistry Letters; vol. 22; nb. 22; (2012); p. 6980 - 6985,6 View in Reaxys NH
O
O
HN N H
N
NH 2
N O
O
NH
Rx-ID: 25696307 View in Reaxys 8/9 Yield
Conditions & References
25 %
1020 : 1-[2-(benzyl-methylamino)ethyl]-3H,7H-pyrrolo[3,2-f]isoquinolin-6-one 1-[2-(benzyl-methylamino)ethyl]-3H,7H-pyrrolo[3,2-f]isoquinolin-6-one A solution of 6-hydrazino-1-isoquinolinone (0.4 g, 1.89 mmol) from Example 3 and 2-(3-(N-methyl-benzylamine)propyl)-1,3-dioxolan (0.668 g, 2.84 mmol) in degassed ethanol (120 ml)/4percent aqueous sulfuric acid (12 ml) was refluxed under nitrogen for six hours. The reaction mixture was concentrated in vacuo and the product purified by flash silica gel chromatography to afford an orange colored solid (0.155 g, 25percent yield). Treatment of the product with ethereal [v. ethanolic?] HCl and crystallization from ethanol ether gave the mono hydrochloride salt as a light amber colored solid (mp=152-155° C.; MW=367.87; HPLC single component). Elemental Analysis for: C21H21N3O 1.0 HCl Calculated: C, 68.56; H, 6.03; N, 11.42 Found: C, 88.62; H, 6.12; N, 11.54 With sulfuric acid, water in ethanol, Time= 6h, Heating / reflux, Fischer Indole Synthesis Patent; Wyeth; US2007/99911; (2007); (A1) English View in Reaxys NH
O O N
HN O
HCl N H
N
NH 2
O NH
Rx-ID: 25770198 View in Reaxys 9/9 Yield 25 %
Conditions & References 1020 :EXAMPLE 1020 1-r2-(benzyl-methylamino)ethvπ-3HJH-pyrrolor3.2-f]isoquinolin-6-oneA solution of 6-hydrazino-1-isoquinolinone (0.4 g, 1.89 mmol) from Example 3 and 2-(3-(N-methyl-benzylamine)propyl)-1 ,3-dioxolan (0.668 g, 2.84 mmol) in degassed ethanol (120 ml)/4percent aqueous sulfuric acid (12 ml) was refluxed under nitrogen for six hours. The reaction mixture was concentrated in vacuo and the product purified by flash silica gel chromatography to afford an orange colored solid <n="82"/>(0.155 g, 25percent yield). Treatment of the product with ethereal [v. ethanollc?] HCI and crystallization from ethanol ether gave the mono hydrochloride salt as a light amber colored solid (mp =
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152-1550C; MW = 367.87; HPLC single component). Elemental Analysis for: C2iH2iN3O 1.0 HCI Calculated: C, 68.56; H, 6.03; N, 11.42 Found: C, 88.62; H, 6.12; N, 11.54 With sulfuric acid in ethanol, water, Time= 6h, Heating / reflux, Fischer Indole Synthesis Patent; WYETH; WO2007/53352; (2007); (A2) English View in Reaxys
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