反応式
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([NH2:12])[N:3]=1.CCN(CC)CC.[F:20][C:21]1([F:36])[O:25][C:24]2[CH:26]=[CH:27][C:28]([C:30]3([C:33](Cl)=[O:34])[CH2:32][CH2:31]3)=[CH:29][C:23]=2[O:22]1>ClCCl>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([NH:12][C:33]([C:30]2([C:28]3[CH:27]=[CH:26][C:24]4[O:25][C:21]([F:36])([F:20])[O:22][C:23]=4[CH:29]=3)[CH2:32][CH2:31]2)=[O:34])[N:3]=1参加物
実験手順
To a solution of 1-bromoisoquinolin-3-amine (3.00 g, 13.5 mmol) and Et3N (3.8 mL, 27 mmol) in dichloromethane (50 mL) was added a solution of 1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarbonyl chloride (4.18 g, 13.5 mmol) in dichloromethane (50 mL). The resulting reaction mixture was allowed to stir at room temperature for 18 h. The reaction mixture was then washed with 1N aqueous NaOH (2×200 mL), 1 N aqueous HCl (1×200 mL) and saturated aqueous NaHCO3 (1×200 mL). The organics were dried over sodium sulfate and evaporated. The resulting material was purified by silica gel chromatography eluting with 0-50% ethyl acetate/hexanes to yield N-(1-bromoisoquinolin-3-yl)-1-(2,2-difluorobenzo[d][1,3]-dioxol-5-yl)cyclopropanecarboxamide (4.2 g, 70%). ESI-MS m/z calc. 446.0. found 447.1 (M+1)+. Retention time 2.39 minutes.
後処理
- customThe resulting reaction mixture
- washThe reaction mixture was then washed with 1N aqueous NaOH (2×200 mL), 1 N aqueous HCl (1×200 mL) and saturated aqueous NaHCO3 (1×200 mL)
- dry with materialThe organics were dried over sodium sulfate
- customevaporated
- customThe resulting material was purified by silica gel chromatography
- washeluting with 0-50% ethyl acetate/hexanes
出典と根拠
- ORDレコード
- ord-cbce805c24bd4b76b4780796e1471d5a
- 出典データセット
- uspto-grants-2014_05
- 特許番号
- US08722704B2
関連ノート
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