m-Chloroperbenzoic acid → HCID 11661826, compound

HRID 1174631Notes

Reaction equation

HRID 1174631 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[CH:12]1([NH:15][C:16](=[O:41])[C:17]2[CH:22]=[C:21]([F:23])[C:20]([CH3:24])=[C:19]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([N:33]4[CH2:38][CH2:37][CH2:36][CH:35]([CH2:39][CH3:40])[CH2:34]4)=[O:32])=[CH:27][N:26]=3)[CH:18]=2)[CH2:14][CH2:13]1>C(Cl)(Cl)Cl.CO>[CH:12]1([NH:15][C:16](=[O:41])[C:17]2[CH:22]=[C:21]([F:23])[C:20]([CH3:24])=[C:19]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([N:33]4[CH2:38][CH2:37][CH2:36][CH:35]([CH2:39][CH3:40])[CH2:34]4)=[O:32])=[CH:27][N+:26]=3[O-:9])[CH:18]=2)[CH2:14][CH2:13]1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 21914621HCID 21914621, compound2×

Product 1

HCID 11661826HCID 11661826, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent2×

Conditions

Temperature
60 °C

Procedure

mCPBA (57-86%, 10 mg) dissolved in chloroform (0.1 ml) was added to a solution of N-cyclopropyl-3-{5-[(3-ethylpiperidin-1-yl)carbonyl]pyridin-2-yl}-5-fluoro-4-methylbenzamide (Intermediate 33, 10.5 mg) in chloroform (2 ml) at 60° C. and the reaction maintained at 60° C. for 5 hrs. The reaction was allowed to cool, diluted with methanol, and passed through an aminopropyl SPE (1 g). The filtrate was reduced to dryness under vacuum and the residue triturated with ether to give N-cyclopropyl-3-{5-[(3-ethyl-1-piperidinyl)carbonyl]-1-oxido-2-pyridinyl}-5-fluoro-4-methylbenzamide as a white solid.

Workup

  1. temperatureto cool
  2. customthe residue triturated with ether

Sources & evidence

ORD record
ord-19a5fa8eee924cefbda00b70d9aa2e44
Source dataset
uspto-grants-2010_11
Patent number
US07838540B2

Reaction notes

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