Sodium Hydroxide → HCID 68492548, compound

HRID 1879226Notes

Reaction equation

HRID 1879226 reaction equation
C([O:3][C:4]([C:6]1[S:10][C:9]([C:11]2[CH:15]=[C:14]([CH3:16])[N:13]([CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[N:12]=2)=[N:8][C:7]=1[CH3:26])=[O:5])C.[OH-].[Na+]>O1CCCC1.O>[F:25][C:22]1[CH:23]=[CH:24][C:19]([CH2:18][CH2:17][N:13]2[C:14]([CH3:16])=[CH:15][C:11]([C:9]3[S:10][C:6]([C:4]([OH:5])=[O:3])=[C:7]([CH3:26])[N:8]=3)=[N:12]2)=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68492370HCID 68492370, compound

Product 1

HCID 68492548HCID 68492548, compoundYield 70.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-{1-[2-(4-fluoro-phenyl)-ethyl]-5-methyl-1H-pyrazol-3-yl}-4-methyl-thiazole-5-carboxylic acid ethyl ester (0.32 g, 0.86 mmol), NaOH (0.17 g, 4.29 mmol) in tetrahydrofuran (5 mL) and water (5 mL) was heated to reflux for 16 hr. The solvent was removed in vacuo and the residue was neutralized with 5% HCl to pH 5-6. The resulting solid was filtered and dried to provide 2-{1-[2-(4-fluoro-phenyl)-ethyl]-5-methyl-1H-pyrazol-3-yl}-4-methyl-thiazole-5-carboxylic acid as a white solid (0.21 g, 70% yield). This material was used without further purification.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 16 hr
  3. customThe solvent was removed in vacuo
  4. filtrationThe resulting solid was filtered
  5. customdried

Sources & evidence

ORD record
ord-b6ea323b5a0a4c659780d01dc127841a
Source dataset
uspto-grants-2012_11
Patent number
US08314138B2

Reaction notes

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