m-Chloroperbenzoic acid → HCID 58487855, compound

HRID 1406385Notes

Reaction equation

HRID 1406385 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][O:13][C:14]1[CH:44]=[CH:43][C:17]([O:18][C:19]2[CH:42]=[CH:41][C:22]([CH2:23][NH:24][C:25]([C:27]3([NH:30][C:31]([C:33]4[CH:34]=[N:35][C:36]([S:39][CH3:40])=[N:37][CH:38]=4)=[O:32])[CH2:29][CH2:28]3)=[O:26])=[CH:21][CH:20]=2)=[C:16]([C:45]([F:48])([F:47])[F:46])[CH:15]=1>ClCCl>[CH3:12][O:13][C:14]1[CH:44]=[CH:43][C:17]([O:18][C:19]2[CH:20]=[CH:21][C:22]([CH2:23][NH:24][C:25]([C:27]3([NH:30][C:31]([C:33]4[CH:34]=[N:35][C:36]([S:39]([CH3:40])=[O:9])=[N:37][CH:38]=4)=[O:32])[CH2:28][CH2:29]3)=[O:26])=[CH:41][CH:42]=2)=[C:16]([C:45]([F:47])([F:48])[F:46])[CH:15]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 66792605HCID 66792605, compound

Product 1

HCID 58487855HCID 58487855, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

186 mg (1.08 mmol) of 3-chloroperbenzoic acid were added at approx. 5° C. to a solution of 575 mg (1.08 mmol) of 2-methylthio-pyrimidine-5-carboxylic acid{1-[4-(4-methoxy-2-trifluoromethyl-phenoxy)-benzylcarbamoyl]-cyclopropyl}-amide (product from Example 144) in 10 mL dichloromethane. Then the cooling was removed and the reaction mixture stirred for a further three hours at ambient temperature. Half the solution was evaporated down and the crude product thus obtained was purified by chromatography (reversed phase HPLC).

Workup

  1. customThen the cooling was removed
  2. customHalf the solution was evaporated down

Sources & evidence

ORD record
ord-411a3415549c4040995ad493a698b77c
Source dataset
uspto-grants-2014_12
Patent number
US08916589B2

Reaction notes

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