Formaldehyde → HCID 11851464, compound

HRID 1641754Notes

Reaction equation

HRID 1641754 reaction equation
[CH3:1][C:2]1[C:7]([CH:8]([S:18]([C:21]2[CH:22]=[N:23][C:24]([C:27]([F:30])([F:29])[F:28])=[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]=[C:4]([C:31]([NH2:33])=[O:32])[CH:3]=1.C=O.[OH-].[Na+].[C:38](OCC)(=[O:40])C>COCCOC>[OH:40][CH2:38][NH:33][C:31]([C:4]1[CH:3]=[C:2]([CH3:1])[C:7]([CH:8]([S:18]([C:21]2[CH:22]=[N:23][C:24]([C:27]([F:30])([F:29])[F:28])=[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:32]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 57736411HCID 57736411, compound

Product 1

HCID 11851464HCID 11851464, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 4-methyl-5-[[[6-(trifluoromethyl)pyridin-3-yl]sulfonyl](2,3,6-trifluorophenyl)methyl]pyridine-2-carboxamide (147 mg, 0.300 mmol) in ethylene glycol dimethyl ether (0.8 ml), an aqueous solution of formaldehyde (37%, 0.200 ml) and 1 N aqueous sodium hydroxide (0.200 ml) were added at room temperature, and the mixture was stirred for 16 hours. Ethyl acetate was added to the reaction mixture, and the mixture was washed with saturated aqueous sodium hydrogencarbonate. The organic layer was dried over anhydrous sodium sulfate and filtered, then the filtrate was concentrated under reduced pressure, and the obtained residue was subjected to flash silica gel chromatography. The fraction obtained from an elution with hexane:ethyl acetate=1:1 was concentrated under reduced pressure, and 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 (113 mg, 0.218 mmol, 73%) as a white solid.

Workup

  1. washthe mixture was washed with saturated aqueous sodium hydrogencarbonate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe fraction obtained from an elution with hexane
  6. concentrationethyl acetate=1:1 was concentrated under reduced pressure
  7. washthe resulting residue was washed with a mixed solvent of ethyl acetate and diethyl ether
  8. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-2bd2eddfbe294436b042192ce6178cf0
Source dataset
uspto-grants-2012_02
Patent number
US08114886B2

Reaction notes

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