Sodium Hydroxide → 2-(1-tert-butyl-5-(4-fluorophenyl)-1H-pyrazol-4-yl)thiazole-4-carboxylic acid

HRID 1750364Notes

Reaction equation

HRID 1750364 reaction equation
[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[C:8]([C:17]2[S:18][CH:19]=[C:20]([C:22]([O:24]CC)=[O:23])[N:21]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C(O)C.C1COCC1>[C:1]([N:5]1[C:9]([C:10]2[CH:11]=[CH:12][C:13]([F:16])=[CH:14][CH:15]=2)=[C:8]([C:17]2[S:18][CH:19]=[C:20]([C:22]([OH:24])=[O:23])[N:21]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86721201ethyl 2-(1-tert-butyl-5-(4-fluorophenyl)-1H-pyrazol-4-yl)thiazole-4-carboxylate

Product 1

HCID 867212022-(1-tert-butyl-5-(4-fluorophenyl)-1H-pyrazol-4-yl)thiazole-4-carboxylic acidYield 95%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixed solution of the compound (0.57 g, 1.53 mmol) obtained in step 1 and 1N aqueous sodium hydroxide solution (2.289 ml, 2.29 mmol) in ethanol (5 mL) and THF (5 mL) was stirred at 60° C. for 3 hr. The reaction mixture was concentrated under reduced pressure, and 1N hydrochloric acid was added to the residue. The precipitate was collected by filtration to give 2-(1-tert-butyl-5-(4-fluorophenyl)-1H-pyrazol-4-yl)thiazole-4-carboxylic acid (0.50 g, 1.448 mmol, 95%) as a white powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and 1N hydrochloric acid
  2. additionwas added to the residue
  3. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-851add3eefea4350bda1300b9546acf5
Source dataset
uspto-grants-2015_10
Patent number
US09156837B2

Reaction notes

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