反応式
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[N:10]1[CH2:15][CH2:14][CH2:13][C:12]2=[C:16]([NH2:20])[N:17]([CH3:19])[N:18]=[C:11]12.C(N(CC)CC)C.[C:28](Cl)(=[O:31])[CH2:29][CH3:30].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[N:10]1[CH2:15][CH2:14][CH2:13][C:12]2=[C:16]([NH:20][C:28](=[O:31])[CH2:29][CH3:30])[N:17]([CH3:19])[N:18]=[C:11]12参加物
反応物 4
生成物 1
試薬・触媒・溶媒 1
反応条件
- 温度
- 0 °C
実験手順
To a stirred solution of 7-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-3-ylamine (5-45; 0.51 g) and triethylamine (0.27 mL) in dichloromethane (40 mL) cooled to 0° C. was added dropwise over 25 minutes a solution of propionyl chloride (0.17 mL) in dichloromethane (10 mL). The resulting mixture was stirred for an additional 1 h at 0° C., followed by 14 h at room temperature. The reaction mixture was stirred with an aqueous 5% citric acid solution (40 mL) for 10 minutes. The layers were separated, and the aqueous layer was further extracted with dichloromethane (50 mL). The combined organic extracts were dried over anhydrous sodium sulfate, decanted from the desiccating agent and concentrated in vacuo. The resulting residue was purified by silica gel chromatography using a dichloromethane/methanol gradient to afford N-[7-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-3-yl]propionamide (7-6; 0.49 g) as an off white solid: ms (MH+)=347.
後処理
- waitfollowed by 14 h at room temperature
- customThe layers were separated
- extractionthe aqueous layer was further extracted with dichloromethane (50 mL)
- dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
- customdecanted from the desiccating agent
- concentrationconcentrated in vacuo
- customThe resulting residue was purified by silica gel chromatography
出典と根拠
- ORDレコード
- ord-326e8be4b5534630b4ad9660aacfb6ba
- 出典データセット
- uspto-grants-2008_10
- 特許番号
- US07432283B2
関連ノート
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