m-Chloroperbenzoic acid → 2-(2-Acetylaminopyridin-4-ylmethylsulfinyl)-N-(3,5-dimethylphenyl)pyridine-3-carboxamide

HRID 1984723Notes

Reaction equation

HRID 1984723 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[C:12]([NH:15][C:16]1[CH:21]=[C:20]([CH2:22][S:23][C:24]2[C:29]([C:30]([NH:32][C:33]3[CH:38]=[C:37]([CH3:39])[CH:36]=[C:35]([CH3:40])[CH:34]=3)=[O:31])=[CH:28][CH:27]=[CH:26][N:25]=2)[CH:19]=[CH:18][N:17]=1)(=[O:14])[CH3:13]>C(Cl)Cl.C(OCC)(=O)C>[C:12]([NH:15][C:16]1[CH:21]=[C:20]([CH2:22][S:23]([C:24]2[C:29]([C:30]([NH:32][C:33]3[CH:34]=[C:35]([CH3:40])[CH:36]=[C:37]([CH3:39])[CH:38]=3)=[O:31])=[CH:28][CH:27]=[CH:26][N:25]=2)=[O:9])[CH:19]=[CH:18][N:17]=1)(=[O:14])[CH3:13]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 111889642-(2-Acetylaminopyridin-4-ylmethylthio)-N-(3,5-dimethylphenyl)pyridine-3-carboxamide

Product 1

HCID 231508782-(2-Acetylaminopyridin-4-ylmethylsulfinyl)-N-(3,5-dimethylphenyl)pyridine-3-carboxamideYield 48%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

m-Chloroperbenzoic acid(75%, 60 mg, 0.26 mmol) was added to a solution of 2-(2-acetylaminopyridin-4-ylmethylthio)-N-(3,5-dimethylphenyl)pyridine-3-carboxamide (Compound No. 4-1, 60 mg, 0.15 mmol) in methylene chloride (3 mL) under ice-cooling, and the mixture was stirred for 1 hour. The reaction mixture was diluted with ethyl acetate (30 mL), the whole was washed with saturated aqueous sodium hydrogen carbonate solution (10 mL) twice and brine (10 mL), and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the precipitated solid was filtered off with ethyl acetate to give 30 mg of the target compound as a colorless solid. (Yield 48%)

Workup

  1. washthe whole was washed with saturated aqueous sodium hydrogen carbonate solution (10 mL) twice
  2. dry with materialbrine (10 mL), and dried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. filtrationthe precipitated solid was filtered off with ethyl acetate

Sources & evidence

ORD record
ord-8bdfe4c71b694f21b3f8c41700195319
Source dataset
uspto-grants-2009_06
Patent number
US07544703B2

Reaction notes

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