Hydrochloric Acid → HCID 68490567, compound

HRID 1879179Notes

Reaction equation

HRID 1879179 reaction equation
C([O:3][C:4]([C:6]1[S:10][C:9]([C:11]2[CH:15]=[CH:14][N:13]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[N:12]=2)=[N:8][C:7]=1[CH3:25])=[O:5])C.[OH-].[Na+].Cl>O1CCCC1.O>[F:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][CH2:16][N:13]2[CH:14]=[CH:15][C:11]([C:9]3[S:10][C:6]([C:4]([OH:5])=[O:3])=[C:7]([CH3:25])[N:8]=3)=[N:12]2)=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68492752HCID 68492752, compound

Product 1

HCID 68490567HCID 68490567, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-{1-[2-(4-fluoro-phenyl)-ethyl]-1H-pyrazol-3-yl}-4-methyl-thiazole-5-carboxylic acid ethyl ester (0.5 g, 1.39 mmol) and NaOH (0.22 g, 5.57 mmol) in tetrahydrofuran (10 mL) and water (5 mL) was heated to reflux for 16 hr. The reaction mixture was cooled to room temperature and neutralized with 5% HCl to pH 6. The precipitate was filtered and dried to provide 2-{1-[2-(4-fluoro-phenyl)-ethyl]-1H-pyrazol-3-yl}-4-methyl-thiazole-5-carboxylic acid (0.40 g, 87%) as a yellow solid. MS (M+H)+=332; Rt=1.04 min.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 16 hr
  3. filtrationThe precipitate was filtered
  4. customdried

Sources & evidence

ORD record
ord-0c315729387d4c468dc9e844e50d3060
Source dataset
uspto-grants-2012_11
Patent number
US08314138B2

Reaction notes

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