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

HRID 1641748
Notes
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Reaction equation

HRID 1641748 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.[CH2:30]=O.Cl.[CH3:33][NH:34][CH3:35].O>CN(C)C=O>[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][CH2:33][N:34]([CH3:30])[CH3:35])=[O:17])=[N:14][CH:15]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 10473Dimethylamine, hydrochlorideHCID 577364915-[(2,5-Difluorophenyl)[(4-fluorophenyl)sulfonyl]methyl]-4-methylpyridine-2-carboxamide

Product 1

HCID 577364565-[(2,5-difluorophenyl)[(4-fluorophenyl)sulfonyl]methyl]-N-(dimethylaminomethyl)-4-methylpyridine-2-carboxamideYield 63%

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, 0.33 mmol) obtained in Example 15 in N,N-dimethylformamide (3 ml), a formaldehyde solution (37%, 54 μl) and dimethylamine hydrochloride (136 mg, 1.67 mmol) were added at 0° C., and the mixture was stirred for 2 hours at room temperature. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate, and was dried over anhydrous sodium 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 dichloromethane:methanol=10:1 was concentrated under reduced pressure, and the resulting residue was washed with diethyl ether and dichloromethane and dried, to obtain the title compound (99 mg, 0.21 mmol, 63%) as a white solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialwas dried over anhydrous sodium sulfate
  3. concentrationThe solvent was concentrated under reduced pressure
  4. customThe fraction obtained from an elution with dichloromethane
  5. concentrationmethanol=10:1 was concentrated under reduced pressure
  6. washthe resulting residue was washed with diethyl ether and dichloromethane
  7. customdried

Sources & evidence

ORD record
ord-a55462c74674461b9dccc5f1b92f632c
Source dataset
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08114886B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes