4-((4-(4-溴-2-氟苯基氨基)-6-甲氧基喹唑啉-7-基氧基)甲基)哌啶-1-羧酸叔丁酯合成路线 （共 15 条）
反应条件
potassium carbonate in N,N-dimethyl-formamide T=20 - 90°C;
参考文献
Gao, Mingzhang; Lola, Christian M.; Wang, Min; Miller, Kathy D.; Sledge, George W.; Zheng, Qi-Huang
Bioorganic and Medicinal Chemistry Letters, 2011 , vol. 21, # 11 p. 3222 - 3226
反应条件
potassium carbonate in N,N-dimethyl-formamide T=95°C; 2 h;
参考文献
AstraZeneca AB
Patent: EP1244647 B1, 2006 ;
Location in patent: Page/Page column 19 ;
EP 1244647 B1
反应条件
1: 4-(4-bromo-2-fluorophenylamino)-7-hydroxy-6-methoxyquinazoline With potassium carbonate in 1-methyl-pyrrolidin-2-one 0.166667 h; 2: 1-(tert-butoxycarbonyl)-4-(4-methylphenylsulphonyloxymethyl)piperidine in 1-methyl-pyrrolidin-2-one T=95°C; 3.5 - 4 h; Product distribution / selectivity;
参考文献
ASTRAZENECA AB; ASTRAZENECA UK LIMITED
Patent: WO2007/36713 A2, 2007 ;
Location in patent: Page/Page column 56; 57 ;
WO 2007/036713 A2
反应条件
di-isopropyl azodicarboxylate; triphenylphosphine in dichloromethane T=20°C; 3 h;
参考文献
HANMI HOLDINGS CO., LTD.; BAE, In Hwan; BYUN, Eun Young; JU, Hae Kyoung; SONG, Ji Young; JUNG, Seung Hyun; JUN, Mi Ae; KIM, Ho Seok; JUNG, Young Hee; SHIM, Mi Yon; AHN, Young Gil; KIM, Maeng Sup
Patent: WO2012/30160 A2, 2012 ;
Location in patent: Page/Page column 52-53 ;
反应条件
1.1: oxalyl dichloride / toluene / 2 h / Reflux 1.2: 2 h 2.1: acetic acid / 0.17 h / 90 °C 2.2: 1 h / Reflux 3.1: 1,4-dioxane / 12 h / Reflux 3.2: 3 h / Reflux 4.1: thionyl chloride; trichlorophosphate / N,N-dimethyl-formamide / 2 h / Reflux 5.1: isopropyl alcohol / 2 h / Reflux 6.1: trifluoroacetic acid / 2 h / Heating 7.1: triphenylphosphine; di-isopropyl azodicarboxylate / dichloromethane / 3 h / 20 °C View Scheme
参考文献
HANMI HOLDINGS CO., LTD.; BAE, In Hwan; BYUN, Eun Young; JU, Hae Kyoung; SONG, Ji Young; JUNG, Seung Hyun; JUN, Mi Ae; KIM, Ho Seok; JUNG, Young Hee; SHIM, Mi Yon; AHN, Young Gil; KIM, Maeng Sup
Patent: WO2012/30160 A2, 2012 ;
反应条件
1.1: potassium permanganate / acetone / 2 h / 30 - 50 °C 2.1: oxalyl dichloride / toluene / 2 h / Reflux 2.2: 2 h 3.1: acetic acid / 0.17 h / 90 °C 3.2: 1 h / Reflux 4.1: 1,4-dioxane / 12 h / Reflux 4.2: 3 h / Reflux 5.1: thionyl chloride; trichlorophosphate / N,N-dimethyl-formamide / 2 h / Reflux 6.1: isopropyl alcohol / 2 h / Reflux 7.1: trifluoroacetic acid / 2 h / Heating 8.1: triphenylphosphine; di-isopropyl azodicarboxylate / dichloromethane / 3 h / 20 °C View Scheme
参考文献
HANMI HOLDINGS CO., LTD.; BAE, In Hwan; BYUN, Eun Young; JU, Hae Kyoung; SONG, Ji Young; JUNG, Seung Hyun; JUN, Mi Ae; KIM, Ho Seok; JUNG, Young Hee; SHIM, Mi Yon; AHN, Young Gil; KIM, Maeng Sup
Patent: WO2012/30160 A2, 2012 ;
反应条件
1.1: acetic acid / 0.17 h / 90 °C 1.2: 1 h / Reflux 2.1: 1,4-dioxane / 12 h / Reflux 2.2: 3 h / Reflux 3.1: thionyl chloride; trichlorophosphate / N,N-dimethyl-formamide / 2 h / Reflux 4.1: isopropyl alcohol / 2 h / Reflux 5.1: trifluoroacetic acid / 2 h / Heating 6.1: triphenylphosphine; di-isopropyl azodicarboxylate / dichloromethane / 3 h / 20 °C View Scheme
参考文献
HANMI HOLDINGS CO., LTD.; BAE, In Hwan; BYUN, Eun Young; JU, Hae Kyoung; SONG, Ji Young; JUNG, Seung Hyun; JUN, Mi Ae; KIM, Ho Seok; JUNG, Young Hee; SHIM, Mi Yon; AHN, Young Gil; KIM, Maeng Sup
Patent: WO2012/30160 A2, 2012 ;
反应条件
1.1: 1,4-dioxane / 12 h / Reflux 1.2: 3 h / Reflux 2.1: thionyl chloride; trichlorophosphate / N,N-dimethyl-formamide / 2 h / Reflux 3.1: isopropyl alcohol / 2 h / Reflux 4.1: trifluoroacetic acid / 2 h / Heating 5.1: triphenylphosphine; di-isopropyl azodicarboxylate / dichloromethane / 3 h / 20 °C View Scheme
参考文献
HANMI HOLDINGS CO., LTD.; BAE, In Hwan; BYUN, Eun Young; JU, Hae Kyoung; SONG, Ji Young; JUNG, Seung Hyun; JUN, Mi Ae; KIM, Ho Seok; JUNG, Young Hee; SHIM, Mi Yon; AHN, Young Gil; KIM, Maeng Sup
Patent: WO2012/30160 A2, 2012 ;
反应条件
1: thionyl chloride; trichlorophosphate / N,N-dimethyl-formamide / 2 h / Reflux 2: isopropyl alcohol / 2 h / Reflux 3: trifluoroacetic acid / 2 h / Heating 4: triphenylphosphine; di-isopropyl azodicarboxylate / dichloromethane / 3 h / 20 °C View Scheme
参考文献
HANMI HOLDINGS CO., LTD.; BAE, In Hwan; BYUN, Eun Young; JU, Hae Kyoung; SONG, Ji Young; JUNG, Seung Hyun; JUN, Mi Ae; KIM, Ho Seok; JUNG, Young Hee; SHIM, Mi Yon; AHN, Young Gil; KIM, Maeng Sup
Patent: WO2012/30160 A2, 2012 ;
反应条件
1.1: nitric acid / 2 h / 0 - 20 °C 2.1: potassium permanganate / acetone / 2 h / 30 - 50 °C 3.1: oxalyl dichloride / toluene / 2 h / Reflux 3.2: 2 h 4.1: acetic acid / 0.17 h / 90 °C 4.2: 1 h / Reflux 5.1: 1,4-dioxane / 12 h / Reflux 5.2: 3 h / Reflux 6.1: thionyl chloride; trichlorophosphate / N,N-dimethyl-formamide / 2 h / Reflux 7.1: isopropyl alcohol / 2 h / Reflux 8.1: trifluoroacetic acid / 2 h / Heating 9.1: triphenylphosphine; di-isopropyl azodicarboxylate / dichloromethane / 3 h / 20 °C View Scheme
参考文献
HANMI HOLDINGS CO., LTD.; BAE, In Hwan; BYUN, Eun Young; JU, Hae Kyoung; SONG, Ji Young; JUNG, Seung Hyun; JUN, Mi Ae; KIM, Ho Seok; JUNG, Young Hee; SHIM, Mi Yon; AHN, Young Gil; KIM, Maeng Sup
Patent: WO2012/30160 A2, 2012 ;
