Methanol → HCID 25002426, compound

HRID 1799381Notes

Reaction equation

HRID 1799381 reaction equation
[OH-:1].[Na+].[CH:3]12[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH:4]1[NH:13][C:14]([C:16]1[CH:17]=[N:18][N:19]([C:25]3[CH:30]=[CH:29][C:28]([C:31]#N)=[CH:27][CH:26]=3)[C:20]=1[C:21]([F:24])([F:23])[F:22])=[O:15])[CH2:10]2.C[OH:34]>>[CH:3]12[CH2:10][CH:9]3[CH2:8][CH:7]([CH2:6][CH:5]([CH2:11]3)[CH:4]1[NH:13][C:14]([C:16]1[CH:17]=[N:18][N:19]([C:25]3[CH:26]=[CH:27][C:28]([C:31]([OH:34])=[O:1])=[CH:29][CH:30]=3)[C:20]=1[C:21]([F:24])([F:23])[F:22])=[O:15])[CH2:12]2

Participants

4

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 67019594HCID 67019594, compound2×

Product 1

HCID 25002426HCID 25002426, compoundYield 93%

Conditions

Temperature
65 °C

Procedure

A solution of Sodium hydroxide (1.056 mL, 2.11 mmol) was added in one portion to a stirred solution of N-adamantan-2-yl-1-(4-cyanophenyl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide (Intermediate #124) (250 mg, 0.60 mmol), in methanol (10 mL) under air. The resulting solution was stirred at 65° C. for 45 hours. The resulting mixture was evaporated to dryness and the residue dissolved in ice/water (25 mL) and the mixture was acidified with 2M HCl. The precipitate was collected by filtration, washed with water (25 mL) and dried under vacuum to afford 4-[4-(adamantan-2-ylcarbamoyl)-5-(trifluoromethyl)-1H-pyrazol-1-yl]benzoic acid (243 mg, 93%) as a white solid, which was used without further purification.

Workup

  1. customThe resulting mixture was evaporated to dryness
  2. dissolutionthe residue dissolved in ice/water (25 mL)
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water (25 mL)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-18cfe5145e21405783a6482f641eec32
Source dataset
uspto-grants-2013_01
Patent number
US08344016B2

Reaction notes

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