Triethylamine → (7R,8aS)-7-[(5-cyclopropylpyrazin-2-yl)oxy]-2-{[2-(trifluoromethyl)phenyl]-sulfonyl}octahydropyrrolo[1,2-a]pyrazine

HRID 240428노트

반응식

HRID 240428 반응식
[CH:1]1([C:4]2[N:5]=[CH:6][C:7]([O:10][C@H:11]3[CH2:19][N:14]4[CH2:15][CH2:16][NH:17][CH2:18][C@@H:13]4[CH2:12]3)=[N:8][CH:9]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.[F:27][C:28]([F:40])([F:39])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[S:35](Cl)(=[O:37])=[O:36]>ClCCl>[CH:1]1([C:4]2[N:5]=[CH:6][C:7]([O:10][C@H:11]3[CH2:19][N:14]4[CH2:15][CH2:16][N:17]([S:35]([C:30]5[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=5[C:28]([F:27])([F:39])[F:40])(=[O:37])=[O:36])[CH2:18][C@@H:13]4[CH2:12]3)=[N:8][CH:9]=2)[CH2:3][CH2:2]1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 1366162-Trifluoromethylbenzenesulphonyl chlorideHCID 86680449(7R,8aS)-7-[(5-cyclopropylpyrazin-2-yl)oxy]octahydropyrrolo[1,2-a]pyrazine

생성물 1

HCID 71544327(7R,8aS)-7-[(5-cyclopropylpyrazin-2-yl)oxy]-2-{[2-(trifluoromethyl)phenyl]-sulfonyl}octahydropyrrolo[1,2-a]pyrazine

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of Example 27B (50 mg, 0.192 mmol) and triethylamine (29.2 mg, 0.288 mmol) in dichloromethane (1 mL) was added 2-(trifluoromethyl)benzene-1-sulfonyl chloride (47 mg, 1.92 mmol). The mixture was stirred at room temperature for 16 hours. The mixture was purified by chromatography on silica gel (ethyl acetate/hexane=4:1) to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.80 (m, 2H), 0.92 (m, 2H), 1.84 (m, 2H), 2.09 (m, 1H), 2.22 (m, 2H), 2.33 (m, 1H), 2.52 (m, 1H), 2.78 (m, 1H), 2.99 (m, 1H), 3.64 (m, 2H), 3.82 (m, 1H), 5.25 (m, 1H), 7.92 (m, 2H), 8.15 (m, 4H); MS (ESI) m/z 469 (M+H)+.

후처리

  1. customThe mixture was purified by chromatography on silica gel (ethyl acetate/hexane=4:1)

출처 및 근거

ORD 기록
ord-d087fbf9ba73434fa9511517b1cb7ac3
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08648074B2

반응 노트

불러오는 중…