Water → N-acetyl-5-[(2,5-difluorophenyl)[(4-fluorophenyl)sulfonyl]methyl]-4-methylpyridine-2-carboxamide

HRID 1641746Notes

Reaction equation

HRID 1641746 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH:9]([S:20]([C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)(=[O:22])=[O:21])[C:10]1[C:11]([CH3:19])=[CH:12][C:13]([C:16]([NH2:18])=[O:17])=[N:14][CH:15]=1.[H-].[Na+].[C:32](OC(=O)C)(=[O:34])[CH3:33].O>CN(C)C=O>[C:32]([NH:18][C:16]([C:13]1[CH:12]=[C:11]([CH3:19])[C:10]([CH:9]([C:3]2[CH:4]=[C:5]([F:8])[CH:6]=[CH:7][C:2]=2[F:1])[S:20]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)(=[O:22])=[O:21])=[CH:15][N:14]=1)=[O:17])(=[O:34])[CH3:33]

Participants

6

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 24758Sodium hydrideHCID 577364915-[(2,5-Difluorophenyl)[(4-fluorophenyl)sulfonyl]methyl]-4-methylpyridine-2-carboxamide

Product 1

HCID 57736484N-acetyl-5-[(2,5-difluorophenyl)[(4-fluorophenyl)sulfonyl]methyl]-4-methylpyridine-2-carboxamideYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-[(2,5-difluorophenyl)[(4-fluorophenyl)sulfonyl]methyl]-4-methylpyridine-2-carboxamide (150 mg, 0.36 mmol) obtained in Example 15 in N,N-dimethylformamide (7 ml), sodium hydride (60%, 34 mg, 0.79 mmol) was added at 0° C., and the mixture was stirred for 1 hour at room temperature. Subsequently, acetic anhydride (40 μl) was added to the reaction solution at 0° C., and the mixture was stirred for 1 hour at room temperature. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate, and was dried over anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography. The fraction obtained from an elution with hexane:ethyl acetate=10:3 was concentrated under reduced pressure, and the resulting residue was washed with diethyl ether and n-hexane, and then was collected by filtration, to obtain the title compound (80 mg, 0.17 mmol, 48%) as a white solid.

Workup

  1. stirringthe mixture was stirred for 1 hour at room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. concentrationThe solvent was concentrated under reduced pressure
  5. customThe fraction obtained from an elution with hexane
  6. concentrationethyl acetate=10:3 was concentrated under reduced pressure
  7. washthe resulting residue was washed with diethyl ether and n-hexane
  8. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-d50e0b11ec9e45188b55a12328b7cd49
Source dataset
uspto-grants-2012_02
Patent number
US08114886B2

Reaction notes

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