Methanol → N-[6-(4-Hydroxycyclohex-1-en-1-yl)-5-methylpyridin-3-yl]-5-methyl-1-[4-(trifluoromethyl)-phenyl]-1H-pyrazole-4-carboxamide

HRID 1748647Notes

Reaction equation

HRID 1748647 reaction equation
[BH4-].[Na+].[CH3:3][C:4]1[CH:5]=[C:6]([NH:17][C:18]([C:20]2[CH:21]=[N:22][N:23]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=3)[CH:24]=2)=[O:19])[CH:7]=[N:8][C:9]=1[C:10]1[CH2:15][CH2:14][C:13](=[O:16])[CH2:12][CH:11]=1.[OH-].[Na+].[CH3:37]O>>[OH:16][CH:13]1[CH2:14][CH2:15][C:10]([C:9]2[N:8]=[CH:7][C:6]([NH:17][C:18]([C:20]3[CH:21]=[N:22][N:23]([C:25]4[CH:26]=[CH:27][C:28]([C:31]([F:34])([F:32])[F:33])=[CH:29][CH:30]=4)[C:24]=3[CH3:37])=[O:19])=[CH:5][C:4]=2[CH3:3])=[CH:11][CH2:12]1

Participants

5

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 86692586N-[5-methyl-6-(4-oxocyclohex-1-en-1-yl)pyridin-3-yl]-1-[4-(trifluoromethyl)phenyl]-1H-pyrazole-4-carboxamide

Product 1

HCID 86692587N-[6-(4-Hydroxycyclohex-1-en-1-yl)-5-methylpyridin-3-yl]-5-methyl-1-[4-(trifluoromethyl)-phenyl]-1H-pyrazole-4-carboxamide

Procedure

Sodium borohydride (19 mg) was added to a solution of N-[5-methyl-6-(4-oxocyclohex-1-en-1-yl)pyridin-3-yl]-1-[4-(trifluoromethyl)phenyl]-1H-pyrazole-4-carboxamide (114 mg) in methanol (15 ml) under ice-cooling and the mixture was stirred at the same temperature for 30 minutes. After the reaction, 1N aqueous solution of sodium hydroxide was added and the organic solvent was evaporated. The precipitated solid was washed with water, filtered and dried at 60° C. under current of air to give the titled compound (110 mg) as a white solid.

Workup

  1. temperaturecooling
  2. additionwas added
  3. customthe organic solvent was evaporated
  4. washThe precipitated solid was washed with water
  5. filtrationfiltered
  6. customdried at 60° C. under current of air

Sources & evidence

ORD record
ord-96899710458242b6a27b7b48bbebeaad
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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