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

HRID 240428Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 240428
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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)+.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-d087fbf9ba73434fa9511517b1cb7ac3
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08648074B2

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