Formaldehyde → HCID 57736483, compound

HRID 1641766Notes

Reaction equation

HRID 1641766 reaction equation
[F:1][CH:2]([F:32])[C:3]1[N:8]=[CH:7][C:6]([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:4]=1.C=O.[OH-].[Na+].[C:37](OCC)(=[O:39])C>COCCOC>[F:32][CH:2]([F:1])[C:3]1[N:8]=[CH:7][C:6]([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][CH2:37][OH:39])=[O:20])=[N:17][CH:18]=2)(=[O:10])=[O:11])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 57736508HCID 57736508, compound

Product 1

HCID 57736483HCID 57736483, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 5-[[[6-(difluoromethyl)pyridin-3-yl]sulfonyl](2,3,6-trifluorophenyl) methyl]-4-methylpyridine-2-carboxamide (90.0 mg, 0.191 mmol) in ethylene glycol dimethyl ether (2 ml), an aqueous solution of formaldehyde (37%, 43.0 μl, 0.573 mmol) and 1 N aqueous sodium hydroxide (9.5 μl) were added at room temperature, and the mixture was stirred for 1 hour. Ethyl acetate was added to the reaction mixture, and the mixture was washed with saturated aqueous ammonium chloride. Subsequently, 1 N hydrochloric acid (5 ml) 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 aqueous sodium hydrogencarbonate and then 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=2:3 was concentrated under reduced pressure. The resulting residue was washed with a mixed solvent of 2-propanol and hexane, and then was collected by filtration, to obtain the title compound (77.0 mg, 0.154 mmol, 80%) as a white solid.

Workup

  1. washthe mixture was washed with saturated aqueous ammonium chloride
  2. additionSubsequently, 1 N hydrochloric acid (5 ml) 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 aqueous sodium hydrogencarbonate
  6. dry with materialwith saturated brine, dried 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=2:3 was concentrated under reduced pressure
  11. washThe resulting residue was washed with a mixed solvent of 2-propanol and hexane
  12. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-95e03ae862424115bdb10b26c24138bf
Source dataset
uspto-grants-2012_02
Patent number
US08114886B2

Reaction notes

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