Triethylamine → N-(1-Acryloyl-piperidin-4-yl)-N-cyclopropyl-3-trifluoromethyl-benzenesulfonamide

HRID 1428953Notes

Reaction equation

[CH:1]1([N:4]([CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)(=[O:7])=[O:6])[CH2:3][CH2:2]1.C(N(CC)CC)C.[C:31](Cl)(=[O:34])[CH:32]=[CH2:33]>C(Cl)Cl>[C:31]([N:21]1[CH2:22][CH2:23][CH:18]([N:4]([CH:1]2[CH2:3][CH2:2]2)[S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:15])[F:16])[CH:9]=2)(=[O:6])=[O:7])[CH2:19][CH2:20]1)(=[O:34])[CH:32]=[CH2:33]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of N-cyclopropyl-N-piperidin-4-yl-3-trifluoromethyl-benzene sulfonamide (1045 mg, 3 mmol) in CH2Cl2 was added triethylamine (0.418 ml, 3 mmmol) and acryloyl chloride (0.244 ml, 3 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 30 min. After quenching with water (5 ml), the mixture was extracted by CHCl3 (50 ml×2), washed with brine (50 ml×2). The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude product was purified by column chromatography on silica gel (AcOEt/n-hexane=4/1) to afford the title compound 1 (648 mg, yield 54%). LC: 100%. MS: m/z=402.39, 403.18 (M+H+).

Workup

customAfter quenching with water (5 ml)
extractionthe mixture was extracted by CHCl3 (50 ml×2)
washwashed with brine (50 ml×2)
dry with materialThe organic layer was dried over Na2SO4
concentrationconcentrated in vacuo
customThe crude product was purified by column chromatography on silica gel (AcOEt/n-hexane=4/1)

Sources & evidence

ORD record: ord-094bd12ee53f4d729d5162502194a3d5
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08937181B2

Reaction notes

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