反応式
[CH3:1][C:2]1[CH:3]=[C:4]([C:8](=O)[CH3:9])[CH:5]=N[CH:7]=1.[NH2:11][C:12]1[CH:13]=[C:14]([C@@H:18]([NH:20][C:21]2[CH:26]=[N:25][CH:24]=[C:23]([Cl:27])[N:22]=2)[CH3:19])[CH:15]=[CH:16][CH:17]=1.[C:28](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.Cl>ClCCCl>[Cl:27][C:23]1[N:22]=[C:21]([NH:20][C@H:18]([C:14]2[CH:15]=[CH:16][CH:17]=[C:12]([NH:11][CH:5]([C:4]3[CH:8]=[CH:9][CH:7]=[C:2]([CH3:1])[CH:3]=3)[CH3:28])[CH:13]=2)[CH3:19])[CH:26]=[N:25][CH:24]=1参加物
反応物 5
生成物 1
試薬・触媒・溶媒 1
反応条件
- 温度
- 80 °C
実験手順
To a solution of 1-(5-methylpyridin-3-yl)ethanone (135 mg, 1 mmol) and N-[(1S)-1-(3-aminophenyl)ethyl]-6-chloropyrazin-2-amine (248 mg, 1 mmol) in 1,2-dichloroethane (5 mL) was added sodium triacetoxyborohydride (300 mg, 1.4 mmol), in one portion, and glacial acetic acid (0.18 mL, 3 mmol). The mixture was heated in the microwave reactor at 80° C. for 1 hour. After this time the mixture was stirred with dilute aqueous hydrochloric acid (2M, 7 mL) for 15 minutes and the two phases were separated. The aqueous phase was basified to pH 9 with solid potassium hydroxide and was extracted with dichloromethane (2×20 mL). The extracts were washed with brine (20 mL), dried (MgSO4) and concentrated under reduced pressure to give an orange oil which was purified by flash chromatography (silica, ethyl acetate/methanol) to give 6-chloro-N-[(1S)-1-(3-{[1-(3-methylphenyl)ethyl]amino}phenyl)ethyl]pyrazin-2-amine (52 mg, 14%) as a pale yellow oil.
後処理
- customthe two phases were separated
- extractionwas extracted with dichloromethane (2×20 mL)
- washThe extracts were washed with brine (20 mL)
- dry with materialdried (MgSO4)
- concentrationconcentrated under reduced pressure
- customto give an orange oil which
- customwas purified by flash chromatography (silica, ethyl acetate/methanol)
出典と根拠
- ORDレコード
- ord-0be33a69c4534afe957e0d5d4eb4bbc3
- 出典データセット
- uspto-grants-2015_05
- 特許番号
- US09029386B2
関連ノート
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