m-Chloroperbenzoic acid → HCID 11689842, compound

HRID 1174629Notes

Reaction equation

HRID 1174629 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:39])[C:21]([CH3:38])=[C:22]([C:24]3[CH:37]=[CH:36][C:27]([C:28]([NH:30][C:31]([CH2:34][CH3:35])([CH3:33])[CH3:32])=[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:39])[C:21]([CH3:38])=[C:22]([C:24]3[N+:25]([O-:9])=[CH:26][C:27]([C:28]([NH:30][C:31]([CH3:33])([CH3:32])[CH2:34][CH3:35])=[O:29])=[CH:36][CH:37]=3)[CH:23]=2)=[O:17])[CH2:14][CH2:13]1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 21914515HCID 21914515, compound2×

Product 1

HCID 11689842HCID 11689842, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

mCPBA (57-86%, 15 mg) was added to a solution of 6-{5-[(cyclopropylamino)carbonyl]-3-fluoro-2-methylphenyl}-N-(tert-pentyl)nicotinamide (Intermediate 32, 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-(1,1-dimethylpropyl)-3-pyridinecarboxamide 1-oxide as a white solid.

Workup

  1. temperatureto cool
  2. customthe residue triturated with ether

Sources & evidence

ORD record
ord-29f1a4b7648d4116a664b62e188ca83f
Source dataset
uspto-grants-2010_11
Patent number
US07838540B2

Reaction notes

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