Formaldehyde → HCID 57736521, compound

HRID 1641761Notes

Reaction equation

HRID 1641761 reaction equation
[CH3:1][O:2]CCOC.[O:7]1[C:11]2[CH:12]=[C:13]([S:16]([CH:19]([C:30]3[C:35]([F:36])=[CH:34][CH:33]=[C:32]([F:37])[C:31]=3[F:38])[C:20]3[C:21]([CH3:29])=[CH:22][C:23]([C:26]([NH2:28])=[O:27])=[N:24][CH:25]=3)(=[O:18])=[O:17])[CH:14]=[CH:15][C:10]=2[CH:9]=[CH:8]1.C=O.[OH-].[Na+]>O>[O:7]1[C:11]2[CH:12]=[C:13]([S:16]([CH:19]([C:30]3[C:35]([F:36])=[CH:34][CH:33]=[C:32]([F:37])[C:31]=3[F:38])[C:20]3[C:21]([CH3:29])=[CH:22][C:23]([C:26]([NH:28][CH2:1][OH:2])=[O:27])=[N:24][CH:25]=3)(=[O:18])=[O:17])[CH:14]=[CH:15][C:10]=2[CH:9]=[CH:8]1

Participants

6

Reactant 4

HCID 712Formaldehyde3×HCID 80711,2-DimethoxyethaneHCID 14798Sodium Hydroxide2×HCID 57736470HCID 57736470, compound

Product 1

HCID 57736521HCID 57736521, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 1,2-dimethoxyethane solution (5 ml) of 5-[(1-benzofuran-6-ylsulfonyl)(2,3,6-trifluorophenyl)methyl]-4-methylpyridine-2-carboxamide (210 mg, 0.457 mmol), an aqueous solution of formaldehyde (37%, 0.111 ml) and 1 N aqueous sodium hydroxide (0.023 ml) were added, and the mixture was stirred for 4 hours at room temperature. An aqueous solution of formaldehyde (37%, 0.111 ml) and 1 N aqueous sodium hydroxide (0.023 ml) were added to the reaction mixture, and the mixture was stirred for 5 hours at room temperature. An aqueous solution of formaldehyde (37%, 0.111 ml) was further added, and then the mixture was stirred for 18 hours at room temperature. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate, and then was washed with water and saturated brine. The mixture was dried over magnesium sulfate and concentrated, and the resulting residue was subjected to flash silica gel column chromatography. The fraction obtained from an elution with hexane:ethyl acetate=2:3 was concentrated. The resulting solid was recrystallized from 2-propanol to obtain the title compound (138 mg, 0.273 mmol, 60%) as a white solid.

Workup

  1. stirringthe mixture was stirred for 5 hours at room temperature
  2. stirringthe mixture was stirred for 18 hours at room temperature
  3. extractionthe mixture was extracted with ethyl acetate
  4. washwas washed with water and saturated brine
  5. dry with materialThe mixture was dried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe fraction obtained from an elution with hexane
  8. concentrationethyl acetate=2:3 was concentrated
  9. customThe resulting solid was recrystallized from 2-propanol

Sources & evidence

ORD record
ord-eb21ae3533d442a99d4ae350defab5b4
Source dataset
uspto-grants-2012_02
Patent number
US08114886B2

Reaction notes

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