N,N-二环丙基-4-[(1,5-二甲基-1H-吡唑-3-基)氨基]-6-乙基-1,6-二氢-1-甲基-咪唑并[4,5-d]吡咯并[2,3-b]吡啶-7-甲酰胺合成路线 （共 12 条）
反应条件
caesium carbonate; 9,9-dimethyl-4,5-bis(diphenyl-phosphino)xanthene; tris-(dibenzylideneacetone)dipalladium(0) in ethylene glycol dimethyl ether T=90°C; 1 h; Inert atmosphere;
参考文献
BRISTOL-MYERS SQUIBB COMPANY; PURANDARE, Ashok V.; GREBINSKI, James W.; HART, Amy; INGHRIM, Jennifer; SCHROEDER, Gretchen; WAN, Honghe
Patent: WO2011/28864 A1, 2011 ;
Location in patent: Page/Page column 112-113 ;
WO 2011/028864 A1
反应条件
1: With acetic acid T=35°C; 4 h; 2: With formic acid T=60°C; 6 h;
参考文献
BRISTOL-MYERS SQUIBB COMPANY; PURANDARE, Ashok V.; GREBINSKI, James W.; HART, Amy; INGHRIM, Jennifer; SCHROEDER, Gretchen; WAN, Honghe
Patent: WO2011/28864 A1, 2011 ;
Location in patent: Page/Page column 111 ;
WO 2011/028864 A1
反应条件
1.1: 3 h / 110 °C 2.1: sodium hexamethyldisilazane / tetrahydrofuran / -78 °C 2.2: -78 - 20 °C 3.1: caesium carbonate; 9,9-dimethyl-4,5-bis(diphenyl-phosphino)xanthene / tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 90 °C 4.1: hydrogenchloride / water; tetrahydrofuran / 0.03 h 5.1: N-iodo-succinimide / acetonitrile / 0.83 h / 0 °C 6.1: tris-(dibenzylideneacetone)dipalladium(0) / isobutyramide / 6 h / 60 °C / Inert atmosphere 7.1: caesium carbonate / N,N-dimethyl-formamide / 1 h / 60 °C 8.1: sodium hydroxide; water / ethanol / 3 h / 60 °C 9.1: 4-(N,N-dimethlyamino)pyridine; 4-methyl-morpholine; HATU / acetonitrile / 5.75 h / 20 - 50 °C 10.1: trifluoroacetic acid / dichloromethane / 0.75 h / 20 °C 11.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C 11.2: 72 h 12.1: acetic acid / 4 h / 35 °C 12.2: 6 h / 60 °C View Scheme
参考文献
WO2011/28864 A1, ;
WO 2011/028864 A1
反应条件
1.1: N-iodo-succinimide / acetonitrile / 0.83 h / 0 °C 2.1: tris-(dibenzylideneacetone)dipalladium(0) / isobutyramide / 6 h / 60 °C / Inert atmosphere 3.1: caesium carbonate / N,N-dimethyl-formamide / 1 h / 60 °C 4.1: sodium hydroxide; water / ethanol / 3 h / 60 °C 5.1: 4-(N,N-dimethlyamino)pyridine; 4-methyl-morpholine; HATU / acetonitrile / 5.75 h / 20 - 50 °C 6.1: trifluoroacetic acid / dichloromethane / 0.75 h / 20 °C 7.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C 7.2: 72 h 8.1: acetic acid / 4 h / 35 °C 8.2: 6 h / 60 °C View Scheme
参考文献
WO2011/28864 A1, ;
WO 2011/028864 A1
反应条件
1.1: tris-(dibenzylideneacetone)dipalladium(0) / isobutyramide / 6 h / 60 °C / Inert atmosphere 2.1: caesium carbonate / N,N-dimethyl-formamide / 1 h / 60 °C 3.1: sodium hydroxide; water / ethanol / 3 h / 60 °C 4.1: 4-(N,N-dimethlyamino)pyridine; 4-methyl-morpholine; HATU / acetonitrile / 5.75 h / 20 - 50 °C 5.1: trifluoroacetic acid / dichloromethane / 0.75 h / 20 °C 6.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C 6.2: 72 h 7.1: acetic acid / 4 h / 35 °C 7.2: 6 h / 60 °C View Scheme
参考文献
WO2011/28864 A1, ;
WO 2011/028864 A1
反应条件
1.1: caesium carbonate / N,N-dimethyl-formamide / 1 h / 60 °C 2.1: sodium hydroxide; water / ethanol / 3 h / 60 °C 3.1: 4-(N,N-dimethlyamino)pyridine; 4-methyl-morpholine; HATU / acetonitrile / 5.75 h / 20 - 50 °C 4.1: trifluoroacetic acid / dichloromethane / 0.75 h / 20 °C 5.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C 5.2: 72 h 6.1: acetic acid / 4 h / 35 °C 6.2: 6 h / 60 °C View Scheme
参考文献
WO2011/28864 A1, ;
WO 2011/028864 A1
反应条件
1.1: sodium hydroxide; water / ethanol / 3 h / 60 °C 2.1: 4-(N,N-dimethlyamino)pyridine; 4-methyl-morpholine; HATU / acetonitrile / 5.75 h / 20 - 50 °C 3.1: trifluoroacetic acid / dichloromethane / 0.75 h / 20 °C 4.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C 4.2: 72 h 5.1: acetic acid / 4 h / 35 °C 5.2: 6 h / 60 °C View Scheme
参考文献
WO2011/28864 A1, ;
WO 2011/028864 A1
反应条件
1.1: 4-(N,N-dimethlyamino)pyridine; 4-methyl-morpholine; HATU / acetonitrile / 5.75 h / 20 - 50 °C 2.1: trifluoroacetic acid / dichloromethane / 0.75 h / 20 °C 3.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C 3.2: 72 h 4.1: acetic acid / 4 h / 35 °C 4.2: 6 h / 60 °C View Scheme
参考文献
WO2011/28864 A1, ;
WO 2011/028864 A1
反应条件
1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C 1.2: 72 h 2.1: acetic acid / 4 h / 35 °C 2.2: 6 h / 60 °C View Scheme
参考文献
WO2011/28864 A1, ;
WO 2011/028864 A1
反应条件
1.1: sodium hexamethyldisilazane / tetrahydrofuran / -78 °C 1.2: -78 - 20 °C 2.1: caesium carbonate; 9,9-dimethyl-4,5-bis(diphenyl-phosphino)xanthene / tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 90 °C 3.1: hydrogenchloride / water; tetrahydrofuran / 0.03 h 4.1: N-iodo-succinimide / acetonitrile / 0.83 h / 0 °C 5.1: tris-(dibenzylideneacetone)dipalladium(0) / isobutyramide / 6 h / 60 °C / Inert atmosphere 6.1: caesium carbonate / N,N-dimethyl-formamide / 1 h / 60 °C 7.1: sodium hydroxide; water / ethanol / 3 h / 60 °C 8.1: 4-(N,N-dimethlyamino)pyridine; 4-methyl-morpholine; HATU / acetonitrile / 5.75 h / 20 - 50 °C 9.1: trifluoroacetic acid / dichloromethane / 0.75 h / 20 °C 10.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C 10.2: 72 h 11.1: acetic acid / 4 h / 35 °C 11.2: 6 h / 60 °C View Scheme
参考文献
WO2011/28864 A1, ;
WO 2011/028864 A1
