Hydrochloric Acid → 2-(3-Phenyl-1h-indazol-1-yl)thiazole-4-carboxylic acid

HRID 1671285Notes

Reaction equation

HRID 1671285 reaction equation
[OH-].[Na+].[C:3]1([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([C:18]3[S:19][CH:20]=[C:21]([C:23]([O:25]CC)=[O:24])[N:22]=3)[N:10]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl>C(O)C>[C:3]1([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([C:18]3[S:19][CH:20]=[C:21]([C:23]([OH:25])=[O:24])[N:22]=3)[N:10]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67059757Ethyl 2-(3-phenyl-1H-indazol-1-yl)thiazole-4-carboxylate

Product 1

HCID 462205002-(3-Phenyl-1h-indazol-1-yl)thiazole-4-carboxylic acidYield 89.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 5 M aqueous solution of sodium hydroxide (10 mL, manufactured by Kanto Chemical Co., Inc.) was added to a solution of the compound of Example 1 (579 mg) in ethanol (10 mL, manufactured by Wako Pure Chemical Industries, Ltd.), and the mixture was stirred for 3 hours at room temperature. 5 M hydrochloric acid (10 mL, manufactured by Kanto Chemical Co., Inc.) was added to the mixture to neutralize the mixture, and then the mixture was extracted with ethyl acetate (3×10 mL), washed with brine (10 mL), and dried (MgSO4). The solvent was then evaporated, to give 477 mg of the title compound. LC-MS: HPLC retention time 5.31 minutes, m/z 322 (M+H), condition A-1.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×10 mL)
  2. washwashed with brine (10 mL)
  3. dry with materialdried (MgSO4)
  4. customThe solvent was then evaporated

Sources & evidence

ORD record
ord-daffd2c9aa33439fa92155d1de531193
Source dataset
uspto-grants-2011_08
Patent number
US07994202B2

Reaction notes

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