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

HRID 2043782Notes

Reaction equation

HRID 2043782 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([N: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.O1CCCC1>[CH3:24][C:23]1[N:19]([CH2:18][C:17]([N:14]2[CH2:13][CH2:12][N:11]([C:8]3[S:9][CH:10]=[C:6]([C:4]([OH:5])=[O:3])[N:7]=3)[CH2:16][CH2:15]2)=[O:29])[N:20]=[C:21]([C:25]([F:28])([F:26])[F:27])[CH:22]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67460845ethyl-2-[4-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-1-piperazinyl]-4-thiazolecarboxylate2×

Product 1

HCID 671510882-[4-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-1-piperazinyl]-4-thiazolecarboxylic acidYield 82.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl-2-[4-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-1-piperazinyl]-4-thiazolecarboxylate (0.83 g, 1.93 mmol) (i.e. the product of Example 30, Step C) in a mixture of methanol (10 mL) and tetrahydrofuran (10 mL) was treated with a 1 N aqueous NaOH solution (4.0 mL, 4.0 mmol). The reaction mixture was stirred at room temperature for 2 h, then treated with 1 N aqueous hydrochloric acid solution (4.5 mL, 4.5 mmol). The resulting mixture was concentrated in vacuo and the resulting suspension was diluted with dichloromethane and filtered to give solid. The resulting solid was washed with dichloromethane and diethyl ether, and air dried to give 0.64 g of the title compound as a white solid.

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. additionthe resulting suspension was diluted with dichloromethane
  3. filtrationfiltered
  4. customto give solid
  5. washThe resulting solid was washed with dichloromethane and diethyl ether, and air
  6. customdried

Sources & evidence

ORD record
ord-bcc16857bb9e4fe7bd991256015553a7
Source dataset
uspto-grants-2013_11
Patent number
US08586611B2

Reaction notes

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