Sodium cyanoborohydride → (S)-5-bromo-1-methyl-3-(5-(2-methyl-4-(oxetan-3-yl)piperazin-1-yl)pyrazin-2-ylamino)pyridin-2(1H)-one
反応式
[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:16]=[N:15][C:14]([N:17]3[CH2:22][CH2:21][NH:20][CH2:19][C@@H:18]3[CH3:23])=[CH:13][N:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.[O:24]1[CH2:27][C:26](=O)[CH2:25]1.[BH3-]C#N.[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:16]=[N:15][C:14]([N:17]3[CH2:22][CH2:21][N:20]([CH:26]4[CH2:27][O:24][CH2:25]4)[CH2:19][C@@H:18]3[CH3:23])=[CH:13][N:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1参加物
6
反応物 3
生成物 1
試薬・触媒・溶媒 2
反応条件
- 温度
- 50 °C
実験手順
A mixture of 230e (2.0 g, 5.3 mmol), oxetan-3-one (763 mg, 10.6 mmol), NaBH3CN (835 mg, 13.3 mmol), and zinc chloride (1.8 g, 13.3 mmol) in methanol (60 mL) was stirred at 50° C. for 30 min. The mixture was concentrated under reduced pressure. To the residue was added water and the resulting mixture was extracted with dichloromethane three times. The combined organic layer was then concentrated under reduced pressure and the resulting residue was purified by silica-gel column chromatography eluting with dichloromethane/methanol (50:1 to 20:1) to afford 230f as a yellow oil (1.6 g, 70%). MS: [M+H]+ 437.2.
後処理
- concentrationThe mixture was concentrated under reduced pressure
- additionTo the residue was added water
- extractionthe resulting mixture was extracted with dichloromethane three times
- concentrationThe combined organic layer was then concentrated under reduced pressure
- customthe resulting residue was purified by silica-gel column chromatography
- washeluting with dichloromethane/methanol (50:1 to 20:1)
出典と根拠
- ORDレコード
- ord-b119e3e4167844caabc4bf0b1ad98c0e
- 出典データセット
- uspto-grants-2016_01
- 特許番号
- US09238655B2
反応ノート
読み込み中…