반응식
[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]=1참가 물질
실험 절차
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.
후처리
- 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
출처 및 근거
- ORD 기록
- ord-cbce805c24bd4b76b4780796e1471d5a
- 출처 데이터셋
- uspto-grants-2014_05
- 특허 번호
- US08722704B2
연결된 노트
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