Formaldehyde → HCID 57736488, compound

HRID 1641758Notes

Reaction equation

HRID 1641758 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:9]([CH:12]([C:23]2[C:28]([F:29])=[CH:27][CH:26]=[C:25]([F:30])[C:24]=2[F:31])[C:13]2[C:14]([CH3:22])=[CH:15][C:16]([C:19]([NH2:21])=[O:20])=[N:17][CH:18]=2)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[F:8].C=O.[OH-].[Na+].[C:36](OCC)(=[O:38])C>COCCOC>[F:1][C:2]1[CH:3]=[C:4]([S:9]([CH:12]([C:23]2[C:28]([F:29])=[CH:27][CH:26]=[C:25]([F:30])[C:24]=2[F:31])[C:13]2[C:14]([CH3:22])=[CH:15][C:16]([C:19]([NH:21][CH2:36][OH:38])=[O:20])=[N:17][CH:18]=2)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 57736540HCID 57736540, compound

Product 1

HCID 57736488HCID 57736488, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 5-[[(3,4-difluorophenyl)sulfonyl](2,3,6-trifluorophenyl)methyl]-4-methylpyridine-2-carboxamide (160 mg, 0.350 mmol) in ethylene glycol dimethyl ether (3 ml), an aqueous solution of formaldehyde (37%, 78.9 μl) and 1 N aqueous sodium hydroxide (17.5 μl) were added at room temperature, and the mixture was stirred for 18 hours. Ethyl acetate was added to the reaction mixture, and the resulting mixture was washed with saturated aqueous ammonium chloride. Subsequently, 1 N hydrochloric acid was added to the organic layer, and the mixture was stirred for 1 hour. After the organic layer was separated, the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and filtered, and then the filtrate was concentrated under reduced pressure. The resulting residue was subjected to flash silica gel chromatography, and the fraction obtained from an elution with hexane:ethyl acetate=1:1 was concentrated under reduced pressure. The resulting residue was washed with a mixed solvent of ethyl acetate and diethyl ether, and then was collected by filtration, to obtain the title compound (100 mg, 0.206 mmol, 59%) as a white solid.

Workup

  1. washthe resulting mixture was washed with saturated aqueous ammonium chloride
  2. additionSubsequently, 1 N hydrochloric acid was added to the organic layer
  3. stirringthe mixture was stirred for 1 hour
  4. customAfter the organic layer was separated
  5. washthe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customthe fraction obtained from an elution with hexane
  10. concentrationethyl acetate=1:1 was concentrated under reduced pressure
  11. washThe resulting residue was washed with a mixed solvent of ethyl acetate and diethyl ether
  12. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-cd95ca10c4c542f5ac33aaddfcc3637a
Source dataset
uspto-grants-2012_02
Patent number
US08114886B2

Reaction notes

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