咪唑并[1,5-a]吡啶-6-羧酸乙酯合成路线 (共 7 条)
反应条件
1: formic acid With acetic anhydride
T=50 - 60°C; 3 h; Inert atmosphere;
2: ethyl 6-(aminomethyl)-3-pyridinecarboxylate hydrochloride T=20°C; 8 h; Inert atmosphere;
3: With sodium hydrogencarbonate in water
参考文献
GLOBAL BLOOD THERAPEUTICS, INC.; CYTOKINETICS, INC.; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; METCALF, Brian; CHUANG, Chihyuan; WARRINGTON, Jeffrey; PAULVANNAN, Kumar; JACOBSON, Matthew P.; HUA, Lan; MORGAN, Bradley
Patent: WO2013/102142 A1, 2013 ;
Location in patent: Paragraph 0149 ;
反应条件
1.1: triethylamine; methanesulfonyl chloride / dichloromethane / 0 °C
1.2: 60 °C
2.1: triphenylphosphine / tetrahydrofuran / 60 °C
3.1: acetic anhydride / 0.5 h / 50 °C
3.2: 20 °C
4.1: trichlorophosphate / toluene / Reflux
View Scheme
参考文献
ShionogiandCo., Ltd.
Patent: EP2341053 A1, 2011 ;
反应条件
1.1: calcium chloride; sodium tetrahydroborate / ethanol / 0.75 h / -5 °C
2.1: triethylamine; methanesulfonyl chloride / dichloromethane / 0 °C
2.2: 60 °C
3.1: triphenylphosphine / tetrahydrofuran / 60 °C
4.1: acetic anhydride / 0.5 h / 50 °C
4.2: 20 °C
5.1: trichlorophosphate / toluene / Reflux
View Scheme
参考文献
ShionogiandCo., Ltd.
Patent: EP2341053 A1, 2011 ;
反应条件
1.1: triphenylphosphine / tetrahydrofuran / 60 °C
2.1: acetic anhydride / 0.5 h / 50 °C
2.2: 20 °C
3.1: trichlorophosphate / toluene / Reflux
View Scheme
参考文献
ShionogiandCo., Ltd.
Patent: EP2341053 A1, 2011 ;
反应条件
1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C / |Inert atmosphere
1.2: |Inert atmosphere
2.1: N,N-dimethylcarbamoyl chloride / dichloromethane / 48 h / 20 °C / |Inert atmosphere
3.1: hydrogenchloride; palladium 10 on activated carbon; hydrogen / water; ethanol / 12 h / |Inert atmosphere
4.1: acetic anhydride / 3 h / 50 - 60 °C / |Inert atmosphere
4.2: 8 h / 20 °C / |Inert atmosphere
View Scheme
参考文献
GLOBAL BLOOD THERAPEUTICS, INC.; CYTOKINETICS, INC.; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; METCALF, Brian; CHUANG, Chihyuan; WARRINGTON, Jeffrey; PAULVANNAN, Kumar; JACOBSON, Matthew P.; HUA, Lan; MORGAN, Bradley
Patent: WO2013/102142 A1, 2013 ;
反应条件
1.1: N,N-dimethylcarbamoyl chloride / dichloromethane / 48 h / 20 °C / |Inert atmosphere
2.1: hydrogenchloride; palladium 10 on activated carbon; hydrogen / water; ethanol / 12 h / |Inert atmosphere
3.1: acetic anhydride / 3 h / 50 - 60 °C / |Inert atmosphere
3.2: 8 h / 20 °C / |Inert atmosphere
View Scheme
参考文献
GLOBAL BLOOD THERAPEUTICS, INC.; CYTOKINETICS, INC.; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; METCALF, Brian; CHUANG, Chihyuan; WARRINGTON, Jeffrey; PAULVANNAN, Kumar; JACOBSON, Matthew P.; HUA, Lan; MORGAN, Bradley
Patent: WO2013/102142 A1, 2013 ;
反应条件
1.1: hydrogenchloride; palladium 10 on activated carbon; hydrogen / water; ethanol / 12 h / |Inert atmosphere
2.1: acetic anhydride / 3 h / 50 - 60 °C / |Inert atmosphere
2.2: 8 h / 20 °C / |Inert atmosphere
View Scheme
参考文献
GLOBAL BLOOD THERAPEUTICS, INC.; CYTOKINETICS, INC.; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; METCALF, Brian; CHUANG, Chihyuan; WARRINGTON, Jeffrey; PAULVANNAN, Kumar; JACOBSON, Matthew P.; HUA, Lan; MORGAN, Bradley
Patent: WO2013/102142 A1, 2013 ;