m-Chloroperbenzoic acid → HCID 11516560, compound

HRID 1174625Notes

Reaction equation

C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[CH:12]1([NH:15][C:16]([C:18]2[CH:19]=[C:20]([F:38])[C:21]([CH3:37])=[C:22]([C:24]3[CH:36]=[CH:35][C:27]([C:28]([NH:30][CH2:31][CH:32]([CH3:34])[CH3:33])=[O:29])=[CH:26][N:25]=3)[CH:23]=2)=[O:17])[CH2:14][CH2:13]1>C(Cl)(Cl)Cl.CO>[CH:12]1([NH:15][C:16]([C:18]2[CH:19]=[C:20]([F:38])[C:21]([CH3:37])=[C:22]([C:24]3[N+:25]([O-:9])=[CH:26][C:27]([C:28]([NH:30][CH2:31][CH:32]([CH3:34])[CH3:33])=[O:29])=[CH:35][CH:36]=3)[CH:23]=2)=[O:17])[CH2:14][CH2:13]1

Participants

Conditions

Temperature: 60 °C

Procedure

mCPBA (57-86%, 15 mg) was added to a solution of 6-(5-cyclopropylcarbamoyl-3-fluoro-2-methyl-phenyl)-N-(2-methylpropyl)-nicotinamide (Intermediate 30, 20 mg) in chloroform (3 ml) at 60° C. and the reaction maintained at 60° C. for 7 hrs. The reaction was allowed to cool, diluted with methanol, and passed through an aminopropyl SPE (2 g) and an SCX SPE (1.0 g). The filtrate was reduced to dryness under vacuum and the residue triturated with ether to give 6-{5-[(cyclopropylamino)carbonyl]-3-fluoro-2-methylphenyl}-N-(2-methylpropyl)-3-pyridinecarboxamide 1 oxide as a white solid.

Workup

temperatureto cool
customthe residue triturated with ether

Sources & evidence

ORD record: ord-3c4ef4d1f66a48959123acde3db13ce0
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07838540B2

Reaction notes

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