反応式
[F:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[NH:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.C[Al](C)C.[NH:22](/[C:26](/[CH3:32])=[CH:27]\[C:28](OC)=[O:29])[C:23]([CH3:25])=O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([N:8]2[C:28](=[O:29])[CH:27]=[C:26]([CH3:32])[N:22]=[C:23]2[CH3:25])[CH:5]=[CH:4][C:3]=1[NH:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1参加物
反応物 3
生成物 1
試薬・触媒・溶媒 1
実験手順
To a solution of 2-fluoro-N1-(2-(piperidin-1-yl)ethyl)benzene-1,4-diamine (1.00 g, 4.21 mmol) in CH2Cl2 (30 mL) was added trimethylaluminium (6.3 mL, 12.6 mmol, 2 M in toluene) slowly. The mixture was stirred at rt for 0.5 h, followed by the addition of a solution of methyl 3-acetaminocrotonate (1.6 g, 10.18 mmol) in CH2Cl2 (8 mL). The reaction mixture was stirred at rt for 24 h, then quenched with saturated NH4Cl aqueous solution and extracted with CH2Cl2 (50 mL×3). The combined organic phases were washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (DCM/MeOH (V/V)=20:1) to give the title compound as a pale yellow solid (0.07 g, 5%). The compound was characterized by the following spectroscopic data:
後処理
- stirringThe reaction mixture was stirred at rt for 24 h
- customquenched with saturated NH4Cl aqueous solution
- extractionextracted with CH2Cl2 (50 mL×3)
- washThe combined organic phases were washed with brine
- dry with materialdried over anhydrous Na2SO4
- concentrationconcentrated in vacuo
- customThe residue was purified by a silica gel column chromatography (DCM/MeOH (V/V)=20:1)
出典と根拠
- ORDレコード
- ord-d63847d5afbd496da4e524cbd75d1849
- 出典データセット
- uspto-grants-2016_09
- 特許番号
- US09434695B2
関連ノート
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