6-氨基-4-(3-氯-4-(吡啶-2-取代甲氧基)苯胺)-7-乙氧基喹啉-3-甲腈合成路线 （共 17 条）
反应条件
1: (E)-4-(dimethylamino)but-2-enoic acid hydrochloride salt With oxalyl dichloride; N,N-dimethyl-formamide in tetrahydrofuran T=0 - 30°C; 2 h; 2: 6-amino-4-[[3-chloro-4-(2-pyridylmethoxy)phenyl]amino]-7-ethoxy-quinoline-3-carbonitrile in tetrahydrofuran; 1-methyl-pyrrolidin-2-one T=0 - 5°C; 3 - 16 h;
参考文献
Wyeth
Patent: US2005/59678 A1, 2005 ;
Location in patent: Page 4 ;
US 20050059678 A1
反应条件
1: (E)-4-(dimethylamino)but-2-enoic acid hydrochloride salt With oxalyl dichloride; N,N-dimethyl-formamide in tetrahydrofuran T=0 - 30°C; 2.25 h; 2: 6-amino-4-[[3-chloro-4-(2-pyridylmethoxy)phenyl]amino]-7-ethoxy-quinoline-3-carbonitrile in tetrahydrofuran; 1-methyl-pyrrolidin-2-one T=0 - 10°C; 20.5 h;
参考文献
Chew, Warren; Papamichelakis, Maria
Patent: US2006/270669 A1, 2006 ;
Location in patent: Page/Page column 19 ;
反应条件
in tetrahydrofuran; 1-methyl-pyrrolidin-2-one T=0 - 5°C; 5 h; Product distribution / selectivity;
参考文献
WYETH
Patent: US2006/270668 A1, 2006 ;
Location in patent: Page/Page column 21 ;
反应条件
1: With methanesulfonic acid in ethanol
6 h; Reflux;
2: With hydrogenchloride; water in ethanol
T=80°C; 19 h;
3: With potassium carbonate in methanol
3 h;
参考文献
MEDOLUTION LIMITED; ZHANG, Dawei
Patent: WO2010/151710 A2, 2010 ;
Location in patent: Page/Page column 33 ;
WO 2010/151710 A2
反应条件
potassium carbonate in methanol; water
pH=9 - 10; 2.5 h;
参考文献
WYETH
Patent: US2006/270668 A1, 2006 ;
Location in patent: Page/Page column 19 ;
反应条件
1.1: benzaldehyde / N,N-dimethyl-formamide / 0.17 h / 20 °C
1.2: 24 h / 50 °C
2.1: pyridine hydrochloride / isopropyl alcohol / Reflux
3.1: hydrogenchloride / water / 5 h / Reflux
View Scheme
参考文献
Carmi, Caterina; Galvani, Elena; Vacondio, Federica; Rivara, Silvia; Lodola, Alessio; Russo, Simonetta; Aiello, Stefania; Bordi, Fabrizio; Costantino, Gabriele; Cavazzoni, Andrea; Alfieri, Roberta R.; Ardizzoni, Andrea; Petronini, Pier Giorgio; Mor, Marco
Journal of Medicinal Chemistry, 2012 , vol. 55, # 5 p. 2251 - 2264
反应条件
1: pyridine hydrochloride / isopropyl alcohol / Reflux
2: hydrogenchloride / water / 5 h / Reflux
View Scheme
参考文献
Carmi, Caterina; Galvani, Elena; Vacondio, Federica; Rivara, Silvia; Lodola, Alessio; Russo, Simonetta; Aiello, Stefania; Bordi, Fabrizio; Costantino, Gabriele; Cavazzoni, Andrea; Alfieri, Roberta R.; Ardizzoni, Andrea; Petronini, Pier Giorgio; Mor, Marco
Journal of Medicinal Chemistry, 2012 , vol. 55, # 5 p. 2251 - 2264
反应条件
1: pyridine hydrochloride / isopropyl alcohol / Reflux
2: hydrogenchloride / water / 5 h / Reflux
View Scheme
参考文献
Carmi, Caterina; Galvani, Elena; Vacondio, Federica; Rivara, Silvia; Lodola, Alessio; Russo, Simonetta; Aiello, Stefania; Bordi, Fabrizio; Costantino, Gabriele; Cavazzoni, Andrea; Alfieri, Roberta R.; Ardizzoni, Andrea; Petronini, Pier Giorgio; Mor, Marco
Journal of Medicinal Chemistry, 2012 , vol. 55, # 5 p. 2251 - 2264
反应条件
1: trichlorophosphate / diethylene glycol dimethyl ether / 100 °C
2: pyridine hydrochloride / isopropyl alcohol / Reflux
3: hydrogenchloride / water / 5 h / Reflux
View Scheme
参考文献
Carmi, Caterina; Galvani, Elena; Vacondio, Federica; Rivara, Silvia; Lodola, Alessio; Russo, Simonetta; Aiello, Stefania; Bordi, Fabrizio; Costantino, Gabriele; Cavazzoni, Andrea; Alfieri, Roberta R.; Ardizzoni, Andrea; Petronini, Pier Giorgio; Mor, Marco
Journal of Medicinal Chemistry, 2012 , vol. 55, # 5 p. 2251 - 2264
反应条件
1.1: benzaldehyde / N,N-dimethyl-formamide / 0.17 h / 20 °C
1.2: 24 h / 50 °C
2.1: pyridine hydrochloride / isopropyl alcohol / Reflux
3.1: hydrogenchloride / water / 5 h / Reflux
View Scheme
参考文献
Carmi, Caterina; Galvani, Elena; Vacondio, Federica; Rivara, Silvia; Lodola, Alessio; Russo, Simonetta; Aiello, Stefania; Bordi, Fabrizio; Costantino, Gabriele; Cavazzoni, Andrea; Alfieri, Roberta R.; Ardizzoni, Andrea; Petronini, Pier Giorgio; Mor, Marco
Journal of Medicinal Chemistry, 2012 , vol. 55, # 5 p. 2251 - 2264
