Methanesulfonyl chloride → HCID 71294192, compound

HRID 240702Notes

Reaction equation

FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[C:17]([C:27]([NH:29][N:30]3[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)=[O:28])[CH:18]=[N:19][C:20]=2[O:21][CH2:22][C:23]([F:26])([F:25])[F:24])=[CH:11][CH:10]=1.C(N(CC)C(C)C)(C)C.[CH3:45][S:46](Cl)(=[O:48])=[O:47]>ClCCl>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[C:17]([C:27]([NH:29][N:30]3[CH2:31][CH2:32][N:33]([S:46]([CH3:45])(=[O:48])=[O:47])[CH2:34][CH2:35]3)=[O:28])[CH:18]=[N:19][C:20]=2[O:21][CH2:22][C:23]([F:24])([F:26])[F:25])=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

5-(4-Chlorophenyl)-N-(piperazin-1-yl)-6-(2,2,2-trifluoroethoxy)-3-pyridinecarboxamide 2,2,2-trifluoroacetate (1:1) (100 mg, 189 μmol) was combined with dichloromethane (5 mL) to give a white suspension. N,N-Diisopropylethylamine (122 mg, 165 μl, 945 μmol) and methanesulfonyl chloride (23.8 mg, 16.1 μl, 208 μmol) were added successively at 0° C. The reaction mixture was stirred for 1 h at 0° C. and subsequently concentrated in vacuo. The residue was purified by flash chromatography (silica gel, 20 g, 0% to 100% ethyl acetate in n-heptane). Recrystallization from ethyl acetate and n-heptane afforded the title compound (50 mg, 54%) as off-white solid; LC-MS (UV peak area/ESI) 98.0%, 493.0916 (M+H)+.

Workup

customto give a white suspension
concentrationsubsequently concentrated in vacuo
customThe residue was purified by flash chromatography (silica gel, 20 g, 0% to 100% ethyl acetate in n-heptane)
customRecrystallization from ethyl acetate and n-heptane

Sources & evidence

ORD record: ord-38c99c46e88d454d9b6fde2dec2c5755
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08648099B2

Reaction notes

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