Isopropanol → N-(3-fluorophenyl)-2-(pyridin-3-ylcarbonyl)-1,2,3,4-tetrahydroisoquinolin-6-amine
反応式
ClC1N=[CH:4][C:5]2[CH2:11][N:10]([C:12]([C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)=[O:13])[CH2:9][CH2:8][C:6]=2N=1.[F:20][C:21]1[CH:22]=[C:23]([CH:25]=[CH:26][CH:27]=1)[NH2:24].CCOC(C)=O.[CH:34](O)([CH3:36])[CH3:35]>>[F:20][C:21]1[CH:22]=[C:23]([NH:24][C:34]2[CH:35]=[C:6]3[C:5](=[CH:4][CH:36]=2)[CH2:11][N:10]([C:12]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)=[O:13])[CH2:9][CH2:8]3)[CH:25]=[CH:26][CH:27]=1参加物
反応条件
- 温度
- 60 °C
実験手順
A solution of (2-chloro-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)(pyridin-3-yl)methanone, Intermediate 5 (0.025 g, 0.091 mmol) in isopropanol (0.1 mL) was treated with 3-fluoroaniline (0.011 g, 0.100 mmol). The resulting mixture was heated to 60° C. and allowed to stir overnight. After being allowed to cool to room temperature EtOAc (10 mL) was added to the reaction mixture, and the resulting solution was then washed twice with brine (10 mL). The combined aqueous layers were washed once with EtOAc (10 mL). The organic layers were combined, then dried over anhydrous Na2SO4(s), filtered and concentrated in vacuo. The resulting crude residue was then purified over silica using a MeOH/CHCl3 gradient. The desired product was obtained in 75.5% yield (0.024 g, 0.069 mmol).
後処理
- additionwas added to the reaction mixture
- washthe resulting solution was then washed twice with brine (10 mL)
- washThe combined aqueous layers were washed once with EtOAc (10 mL)
- dry with materialdried over anhydrous Na2SO4(s)
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe resulting crude residue was then purified over silica using a MeOH/CHCl3 gradient
出典と根拠
- ORDレコード
- ord-fb783abb8e5c4712b357f7e770251002
- 出典データセット
- uspto-grants-2016_03
- 特許番号
- US09296747B1
反応ノート
読み込み中…