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

HRID 240428Notes

Reaction equation

HRID 240428 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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)+.

Workup

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

Sources & evidence

ORD record
ord-d087fbf9ba73434fa9511517b1cb7ac3
Source dataset
uspto-grants-2014_02
Patent number
US08648074B2

Reaction notes

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