Methanol → HCID 57736470, compound

HRID 1641760Notes

Reaction equation

HRID 1641760 reaction equation
[O:1]1[C:5]2[CH:6]=[C:7]([S:10][CH:11]([C:22]3[C:27]([F:28])=[CH:26][CH:25]=[C:24]([F:29])[C:23]=3[F:30])[C:12]3[C:13]([CH3:21])=[CH:14][C:15]([C:18]([NH2:20])=[O:19])=[N:16][CH:17]=3)[CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1.[OH2:31].C[OH:33]>C(OCC)(=O)C.OO>[O:1]1[C:5]2[CH:6]=[C:7]([S:10]([CH:11]([C:22]3[C:27]([F:28])=[CH:26][CH:25]=[C:24]([F:29])[C:23]=3[F:30])[C:12]3[C:13]([CH3:21])=[CH:14][C:15]([C:18]([NH2:20])=[O:19])=[N:16][CH:17]=3)(=[O:33])=[O:31])[CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

6

Reactant 3

HCID 887MethanolHCID 962WaterHCID 57736446HCID 57736446, compound

Product 1

HCID 57736470HCID 57736470, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 784Hydrogen PeroxideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-[(1-benzofuran-6-ylthio)(2,3,6-trifluorophenyl)methyl]-4-methylpyridine-2-carboxamide (93.0 mg, 0.217 mmol) in ethyl acetate (5 ml) and methanol (5 ml), 30% aqueous hydrogen peroxide (2.5 ml) and hexaammonium heptamolybdate tetrahydrate (10 mg, 0.00809 mmol) were added, and the mixture was stirred for 9 hours at room temperature. Hexaammonium heptamolybdate tetrahydrate (10 mg, 0.00809 mmol) was added to the reaction mixture, and the mixture was stirred for 16 hours at room temperature. Furthermore, 30 aqueous hydrogen peroxide (1.0 ml) was added to the reaction mixture, and the resulting mixture was stirred for 3 hours. Water was added to the reaction mixture, and the organic solvent was distilled off under reduced pressure. The resulting residue was extracted with ethyl acetate, and was washed sequentially with water, sodium thiosulfate, water and saturated brine. The residue was dried over magnesium sulfate, and then was concentrated. The resulting residue was subjected to flash silica gel column chromatography, and the fraction obtained from an elution with hexane:ethyl acetate=2:3 was concentrated. The resulting solid was recrystallized from ethyl acetate to obtain the title compound (35.8 mg, 0.0778 mmol, 36%) as a white solid.

Workup

  1. stirringthe mixture was stirred for 16 hours at room temperature
  2. stirringthe resulting mixture was stirred for 3 hours
  3. distillationthe organic solvent was distilled off under reduced pressure
  4. extractionThe resulting residue was extracted with ethyl acetate
  5. washwas washed sequentially with water, sodium thiosulfate, water and saturated brine
  6. dry with materialThe residue was dried over magnesium sulfate
  7. concentrationwas concentrated
  8. customthe fraction obtained from an elution with hexane
  9. concentrationethyl acetate=2:3 was concentrated
  10. customThe resulting solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-ed459abd0a524ce39f0297250b965d13
Source dataset
uspto-grants-2012_02
Patent number
US08114886B2

Reaction notes

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