(2S)-1-[4-[2-[6-氨基-8-[(6-溴-1,3-苯并二氧戊环-5-基)硫基]-9H-嘌呤-9-基]乙基]-1-哌啶基]-2-羟基-1-丙酮合成路线 （共 17 条）
反应条件
1: potassium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 9,9-dimethyl-4,5-bis(diphenyl-phosphino)xanthene / 1,4-dioxane / 16 h / 100 °C / |Inert atmosphere
2: 2-(tert-butyl)-1,1,3,3-tetramethylguanidine / N,N-dimethyl-formamide / 10 h / 80 °C
3: trifluoroacetic acid / dichloromethane / 2 h / 10 - 20 °C
4: triethylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran; N,N-dimethyl-formamide / 10 h / 20 °C
View Scheme
参考文献
Kim, Se-Ho; Bajji, Ashok; Tangallapally, Rajendra; Markovitz, Benjamin; Trovato, Richard; Shenderovich, Mark; Baichwal, Vijay; Bartel, Paul; Cimbora, Daniel; McKinnon, Rena; Robinson, Rosann; Papac, Damon; Wettstein, Daniel; Carlson, Robert; Yager, Kraig M.
Journal of Medicinal Chemistry, 2012 , vol. 55, # 17 p. 7480 - 7501
反应条件
1: tris-(dibenzylideneacetone)dipalladium(0); 9,9-dimethyl-4,5-bis(diphenyl-phosphino)xanthene; N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 10 h / 100 °C / |Inert atmosphere
2: boron trifluoride diethyl etherate; N-bromosuccinmide / acetonitrile / -15 - 5 °C
3: sodium ethanolate / tetrahydrofuran; ethanol / 2 h / 20 °C
4: tetrahydrofuran / 10 h / 70 °C
5: trifluoroacetic acid / dichloromethane / 2 h / 10 - 20 °C
6: triethylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran; N,N-dimethyl-formamide / 10 h / 20 °C
View Scheme
参考文献
Kim, Se-Ho; Bajji, Ashok; Tangallapally, Rajendra; Markovitz, Benjamin; Trovato, Richard; Shenderovich, Mark; Baichwal, Vijay; Bartel, Paul; Cimbora, Daniel; McKinnon, Rena; Robinson, Rosann; Papac, Damon; Wettstein, Daniel; Carlson, Robert; Yager, Kraig M.
Journal of Medicinal Chemistry, 2012 , vol. 55, # 17 p. 7480 - 7501
反应条件
1: sodium ethanolate / tetrahydrofuran; ethanol / 2 h / 20 °C
2: tetrahydrofuran / 10 h / 70 °C
3: trifluoroacetic acid / dichloromethane / 2 h / 10 - 20 °C
4: triethylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran; N,N-dimethyl-formamide / 10 h / 20 °C
View Scheme
参考文献
Kim, Se-Ho; Bajji, Ashok; Tangallapally, Rajendra; Markovitz, Benjamin; Trovato, Richard; Shenderovich, Mark; Baichwal, Vijay; Bartel, Paul; Cimbora, Daniel; McKinnon, Rena; Robinson, Rosann; Papac, Damon; Wettstein, Daniel; Carlson, Robert; Yager, Kraig M.
Journal of Medicinal Chemistry, 2012 , vol. 55, # 17 p. 7480 - 7501
反应条件
1: boron trifluoride diethyl etherate; N-bromosuccinmide / acetonitrile / -15 - 5 °C
2: sodium ethanolate / tetrahydrofuran; ethanol / 2 h / 20 °C
3: tetrahydrofuran / 10 h / 70 °C
4: trifluoroacetic acid / dichloromethane / 2 h / 10 - 20 °C
5: triethylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran; N,N-dimethyl-formamide / 10 h / 20 °C
View Scheme
参考文献
Kim, Se-Ho; Bajji, Ashok; Tangallapally, Rajendra; Markovitz, Benjamin; Trovato, Richard; Shenderovich, Mark; Baichwal, Vijay; Bartel, Paul; Cimbora, Daniel; McKinnon, Rena; Robinson, Rosann; Papac, Damon; Wettstein, Daniel; Carlson, Robert; Yager, Kraig M.
Journal of Medicinal Chemistry, 2012 , vol. 55, # 17 p. 7480 - 7501
反应条件
1.1: caesium carbonate / N,N-dimethyl-formamide / 12 h / 20 °C
2.1: tetrahydrofuran; methanol / 20 °C / NaOAc-AcOH buffer
2.2: 2 h / 20 °C
3.1: silver carbonate / N,N-dimethyl-formamide / 100 °C
4.1: bromine / acetic acid / 1 h / 20 °C
4.2: 1 h
5.1: triethylamine / dichloromethane; tetrahydrofuran / 20 °C
5.2: 6 h
View Scheme
参考文献
MYREXIS, INC.; BAJJI, Ashok, C.; TANGALLAPALLY, Rajendra, P.; KIM, In, Chul; KIM, Se, Ho; PARKER, Daniel, P.; TROVATO, Richard; PAPAC, Damon, I.; YAGER, Kraig; BAICHWAL, Vijay, R.
Patent: WO2012/148550 A1, 2012 ;
反应条件
1.1: caesium carbonate / N,N-dimethyl-formamide / 12 h / 20 °C
2.1: tetrahydrofuran; methanol / 20 °C / NaOAc-AcOH buffer
2.2: 2 h / 20 °C
3.1: silver carbonate / N,N-dimethyl-formamide / 100 °C
4.1: bromine / acetic acid / 1 h / 20 °C
4.2: 1 h
5.1: triethylamine / dichloromethane; tetrahydrofuran / 20 °C
5.2: 6 h
View Scheme
参考文献
MYREXIS, INC.; BAJJI, Ashok, C.; TANGALLAPALLY, Rajendra, P.; KIM, In, Chul; KIM, Se, Ho; PARKER, Daniel, P.; TROVATO, Richard; PAPAC, Damon, I.; YAGER, Kraig; BAICHWAL, Vijay, R.
Patent: WO2012/148550 A1, 2012 ;
反应条件
1.1: tetrahydrofuran; methanol / 20 °C / NaOAc-AcOH buffer
1.2: 2 h / 20 °C
2.1: silver carbonate / N,N-dimethyl-formamide / 100 °C
3.1: bromine / acetic acid / 1 h / 20 °C
3.2: 1 h
4.1: triethylamine / dichloromethane; tetrahydrofuran / 20 °C
4.2: 6 h
View Scheme
参考文献
MYREXIS, INC.; BAJJI, Ashok, C.; TANGALLAPALLY, Rajendra, P.; KIM, In, Chul; KIM, Se, Ho; PARKER, Daniel, P.; TROVATO, Richard; PAPAC, Damon, I.; YAGER, Kraig; BAICHWAL, Vijay, R.
Patent: WO2012/148550 A1, 2012 ;
