Hydrochloric Acid → 2-[1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-4-thiazolecarboxylic acid

HRID 1966948Notes

Reaction equation

HRID 1966948 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([CH:11]2[CH2:16][CH2:15][N:14]([C:17](=[O:29])[CH2:18][N:19]3[C:23]([CH3:24])=[CH:22][C:21]([C:25]([F:28])([F:27])[F:26])=[N:20]3)[CH2:13][CH2:12]2)[S:9][CH:10]=1)=[O:5])C.[OH-].[Na+].Cl>CO>[CH3:24][C:23]1[N:19]([CH2:18][C:17]([N:14]2[CH2:15][CH2:16][CH:11]([C:8]3[S:9][CH:10]=[C:6]([C:4]([OH:5])=[O:3])[N:7]=3)[CH2:12][CH2:13]2)=[O:29])[N:20]=[C:21]([C:25]([F:28])([F:26])[F:27])[CH:22]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66911511ethyl-2-[1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-4-thiazolecarboxylate2×

Product 1

HCID 666014572-[1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-4-thiazolecarboxylic acidYield 90.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred solution of ethyl-2-[1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-4-thiazolecarboxylate (13.0 g, 30.2 mmol) (i.e. the product of Example 2, Step B) in methanol (60 mL) was cooled to 0° C. and treated with an aqueous sodium hydroxide solution (1 N, 36.3 mL, 36.3 mmol). The stirred reaction mixture was allowed to warm to room temperature for 5 h. The reaction mixture was cooled again to 0° C. and treated with aqueous hydrochloric acid (1 N, 36.3 mL, 36.3 mmol). The resulting precipitate was collected under filtration, washed with water and dried in a vacuum oven at 100° C. to give 10.95 g of the title compound as a white solid.

Workup

  1. customThe stirred reaction mixture
  2. temperatureThe reaction mixture was cooled again to 0° C.
  3. filtrationThe resulting precipitate was collected under filtration
  4. washwashed with water
  5. customdried in a vacuum oven at 100° C.

Sources & evidence

ORD record
ord-a2ecbf0112494de1a13b57941d0ddf61
Source dataset
uspto-grants-2013_04
Patent number
US08420673B2

Reaction notes

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