Formaldehyde → 5-[(2,5-difluorophenyl)[(4-fluorophenyl)sulfonyl]methyl]-N-(1-hydroxymethyl)-4-methylpyridine-2-carboxamide

HRID 1641731Notes

Reaction equation

HRID 1641731 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.C=O.[OH-].[Na+].[C:34](=O)([O-])[O-:35].[Na+].[Na+]>COCCOC>[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]([NH:18][CH2:34][OH:35])=[O:17])=[N:14][CH:15]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 577364915-[(2,5-Difluorophenyl)[(4-fluorophenyl)sulfonyl]methyl]-4-methylpyridine-2-carboxamide

Product 1

HCID 119996905-[(2,5-difluorophenyl)[(4-fluorophenyl)sulfonyl]methyl]-N-(1-hydroxymethyl)-4-methylpyridine-2-carboxamideYield 153.7%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 5-[(2,5-difluorophenyl)[(4-fluorophenyl)sulfonyl]methyl]-4-methylpyridine-2-carboxamide (744 mg, 1.84 mmol) obtained in Example 15 in ethylene glycol dimethyl ether (8 ml), an aqueous solution of formaldehyde (37%, 0.4 ml) and 5% aqueous sodium hydroxide (1.6 ml) were added at 0° C., and the resulting mixture was stirred for 3 hours at room temperature. Sodium carbonate (80 mg) was added to the reaction mixture, and the mixture was stirred for 10 minutes at room temperature. The mixture was concentrated under reduced pressure, and then the residue was dissolved in chloroform, dried over magnesium sulfate, and filtered. Subsequently, the filtrate was concentrated under reduced pressure, and the resulting residue was washed with diethyl ether, and then was collected by filtration, to obtain the title compound (524 mg, 1.16 mmol, 63%) as a white solid.

Workup

  1. stirringthe mixture was stirred for 10 minutes at room temperature
  2. concentrationThe mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in chloroform
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationSubsequently, the filtrate was concentrated under reduced pressure
  7. washthe resulting residue was washed with diethyl ether
  8. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-a25e7fd878164982a4368131c76fcbc7
Source dataset
uspto-grants-2012_02
Patent number
US08114886B2

Reaction notes

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