Formaldehyde → HCID 57736529, compound

HRID 1641759Notes

Reaction equation

HRID 1641759 reaction equation
[CH3:1][C:2]1[C:7]([CH:8]([S:18]([C:21]2[CH:26]=[CH:25][C:24]([O:27][C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[C:9]2[C:14]([F:15])=[CH:13][CH:12]=[C:11]([F:16])[C:10]=2[F:17])=[CH:6][N:5]=[C:4]([C:32]([NH2:34])=[O:33])[CH:3]=1.C=O.[OH-].[Na+].[C:39](OCC)(=[O:41])C>COCCOC>[OH:41][CH2:39][NH:34][C:32]([C:4]1[CH:3]=[C:2]([CH3:1])[C:7]([CH:8]([S:18]([C:21]2[CH:22]=[CH:23][C:24]([O:27][C:28]([F:31])([F:29])[F:30])=[CH:25][CH:26]=2)(=[O:20])=[O:19])[C:9]2[C:14]([F:15])=[CH:13][CH:12]=[C:11]([F:16])[C:10]=2[F:17])=[CH:6][N:5]=1)=[O:33]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 57736408HCID 57736408, compound

Product 1

HCID 57736529HCID 57736529, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 4-methyl-5-[[[4-(trifluoromethoxy)phenyl]sulfonyl](2,3,6-trifluorophenyl) methyl]pyridine-2-carboxamide (177 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 2 days. Ethyl acetate was added to the reaction mixture, and the 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 (59.4 mg, 0.111 mmol, 32%) as a white solid.

Workup

  1. washthe 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-71d9af9b6ac3425589e5c1516e278be0
Source dataset
uspto-grants-2012_02
Patent number
US08114886B2

Reaction notes

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