N-(3-氨基-2,4-二氟苯基)丙烷-1-磺酰胺合成路线 （共 10 条）
反应条件
1: With diphenyl phosphoryl azide; triethylamine in tetrahydrofuran
T=20 - 80°C; 5 h;
2: With water in tetrahydrofuran
T=80°C; Curtius Rearrangement; 15 h;
参考文献
ARRAY BIOPHARMA INC.; GENENTECH, INC.; ALIAGAS, Ignacio; GRADL, Stefan; GUNZNER, Janet; MATHIEU, Simon; RUDOLPH, Joachim; WEN, Zhaoyang; WENGLOWSKY, Steven Mark
Patent: WO2011/25947 A1, 2011 ;
Location in patent: Page/Page column 44 ;
WO 2011/025947 A1
反应条件
trifluoroacetic acid in dichloromethane
T=20°C;
参考文献
PLEXXIKON INC.
Patent: WO2009/12283 A1, 2009 ;
Location in patent: Page/Page column 94-95 ;
WO 2009/012283 A1
反应条件
1.1: hydrogen / palladium 10 on activated carbon / ethanol / Inert atmosphere
2.1: triethylamine / dichloromethane / 1 h / 20 °C / Cooling with water bath
3.1: sodium hydroxide; water / tetrahydrofuran; methanol / 20 °C
4.1: triethylamine; diphenyl phosphoryl azide / tetrahydrofuran / 5 h / 20 - 80 °C
4.2: 15 h / 80 °C
View Scheme
参考文献
ARRAY BIOPHARMA INC.; GENENTECH, INC.; ALIAGAS, Ignacio; GRADL, Stefan; GUNZNER, Janet; LEE, Wendy; MATHIEU, Simon; RUDOLPH, Joachim; WEN, Zhaoyang; ZHAO, Guiling; BUCKMELTER, Alexandre J.; GRINA, Jonas; HANSEN, Joshua D.; LAIRD, Ellen; MORENO, David; REN, Li; WENGLOWSKY, Steven Mark
Patent: WO2011/25938 A2, 2011 ;
WO 2011/025938 A2
反应条件
1.1: methanol / 2 h / Cooling with water bath
2.1: hydrogen / palladium 10 on activated carbon / ethanol / Inert atmosphere
3.1: triethylamine / dichloromethane / 1 h / 20 °C / Cooling with water bath
4.1: sodium hydroxide; water / tetrahydrofuran; methanol / 20 °C
5.1: triethylamine; diphenyl phosphoryl azide / tetrahydrofuran / 5 h / 20 - 80 °C
5.2: 15 h / 80 °C
View Scheme
参考文献
ARRAY BIOPHARMA INC.; GENENTECH, INC.; ALIAGAS, Ignacio; GRADL, Stefan; GUNZNER, Janet; LEE, Wendy; MATHIEU, Simon; RUDOLPH, Joachim; WEN, Zhaoyang; ZHAO, Guiling; BUCKMELTER, Alexandre J.; GRINA, Jonas; HANSEN, Joshua D.; LAIRD, Ellen; MORENO, David; REN, Li; WENGLOWSKY, Steven Mark
Patent: WO2011/25938 A2, 2011 ;
WO 2011/025938 A2
反应条件
1.1: triethylamine / dichloromethane / 1 h / 20 °C / Cooling with water bath
2.1: sodium hydroxide; water / tetrahydrofuran; methanol / 20 °C
3.1: triethylamine; diphenyl phosphoryl azide / tetrahydrofuran / 5 h / 20 - 80 °C
3.2: 15 h / 80 °C
View Scheme
参考文献
ARRAY BIOPHARMA INC.; GENENTECH, INC.; ALIAGAS, Ignacio; GRADL, Stefan; GUNZNER, Janet; LEE, Wendy; MATHIEU, Simon; RUDOLPH, Joachim; WEN, Zhaoyang; ZHAO, Guiling; BUCKMELTER, Alexandre J.; GRINA, Jonas; HANSEN, Joshua D.; LAIRD, Ellen; MORENO, David; REN, Li; WENGLOWSKY, Steven Mark
Patent: WO2011/25938 A2, 2011 ;
WO 2011/025938 A2
反应条件
1.1: sodium hydroxide; water / tetrahydrofuran; methanol / 20 °C
2.1: triethylamine; diphenyl phosphoryl azide / tetrahydrofuran / 5 h / 20 - 80 °C
2.2: 15 h / 80 °C
View Scheme
参考文献
ARRAY BIOPHARMA INC.; GENENTECH, INC.; ALIAGAS, Ignacio; GRADL, Stefan; GUNZNER, Janet; LEE, Wendy; MATHIEU, Simon; RUDOLPH, Joachim; WEN, Zhaoyang; ZHAO, Guiling; BUCKMELTER, Alexandre J.; GRINA, Jonas; HANSEN, Joshua D.; LAIRD, Ellen; MORENO, David; REN, Li; WENGLOWSKY, Steven Mark
Patent: WO2011/25938 A2, 2011 ;
WO 2011/025938 A2
反应条件
1.1: hydrogen / palladium 10 on activated carbon / methanol / 3 h / 10343.2 Torr / autoclave
2.1: pyridine / dichloromethane / 16 h / 20 °C
3.1: hydrogenchloride / ethanol; water / 2 h / 80 °C
3.2: pH 6
View Scheme
参考文献
BOEHRINGER INGELHEIM INTERNATIONAL GMBH; STADTMUELLER, Heinz
Patent: WO2012/104388 A1, 2012 ;
WO 2012/104388 A1
反应条件
1.1: sulfuric acid / 2 h / 20 °C
2.1: palladium 10 on activated carbon; hydrogen / methanol / 20 °C
3.1: pyridine / 1,2-dichloro-ethane / 5 h / 100 °C
4.1: lithium hydroxide hydrate; water / tetrahydrofuran / 20 °C
5.1: triethylamine; diphenyl phosphoryl azide / tetrahydrofuran / 5 h / 20 - 80 °C
5.2: 80 °C
View Scheme
参考文献
CENTAURUS BIOPHARMA CO., LTD.; XIAO, Dengming; LI, Jijun; ZHU, Yan; HU, Yuandong; WANG, Huting; WANG, Zhe; WANG, Zanping; WEI, Yongheng; SUN, Yinghui; WU, Qiong; ZHANG, Hui; PENG, Yong; KONG, Fansheng; SUN, Ying; LUO, Hong; HAN, Yongxin
Patent: WO2013/71865 A1, 2013 ;
反应条件
1.1: lithium hydroxide hydrate; water / tetrahydrofuran / 20 °C
2.1: triethylamine; diphenyl phosphoryl azide / tetrahydrofuran / 5 h / 20 - 80 °C
2.2: 80 °C
View Scheme
参考文献
CENTAURUS BIOPHARMA CO., LTD.; XIAO, Dengming; LI, Jijun; ZHU, Yan; HU, Yuandong; WANG, Huting; WANG, Zhe; WANG, Zanping; WEI, Yongheng; SUN, Yinghui; WU, Qiong; ZHANG, Hui; PENG, Yong; KONG, Fansheng; SUN, Ying; LUO, Hong; HAN, Yongxin
Patent: WO2013/71865 A1, 2013 ;
反应条件
1.1: thionyl chloride / 2 h / |Reflux
1.2: 2 h / 20 °C
2.1: sulfuric acid / 2 h / 20 °C
3.1: palladium 10 on activated carbon; hydrogen / methanol / 20 °C
4.1: pyridine / 1,2-dichloro-ethane / 5 h / 100 °C
5.1: lithium hydroxide hydrate; water / tetrahydrofuran / 20 °C
6.1: triethylamine; diphenyl phosphoryl azide / tetrahydrofuran / 5 h / 20 - 80 °C
6.2: 80 °C
View Scheme
参考文献
CENTAURUS BIOPHARMA CO., LTD.; XIAO, Dengming; LI, Jijun; ZHU, Yan; HU, Yuandong; WANG, Huting; WANG, Zhe; WANG, Zanping; WEI, Yongheng; SUN, Yinghui; WU, Qiong; ZHANG, Hui; PENG, Yong; KONG, Fansheng; SUN, Ying; LUO, Hong; HAN, Yongxin
Patent: WO2013/71865 A1, 2013 ;
