Hydrochloric Acid → 5-(4-(4-chlorobenzyl)-2-(pyridin-4-yl)thiazol-5-yl)-1H-pyrazole-3-carboxylic acid

HRID 2401838Notes

Reaction equation

HRID 2401838 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][C:7]2[N:8]=[C:9]([C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)[S:10][C:11]=2[C:12]2[NH:16][N:15]=[C:14]([C:17]([O:19]CC)=[O:18])[CH:13]=2)=[CH:4][CH:3]=1.[Li+].[OH-].Cl>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[N:8]=[C:9]([C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)[S:10][C:11]=2[C:12]2[NH:16][N:15]=[C:14]([C:17]([OH:19])=[O:18])[CH:13]=2)=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66749559ethyl 5-(4-(4-chlorobenzyl)-2-(pyridin-4-yl)thiazol-5-yl)-1H-pyrazole-3-carboxylate

Product 1

HCID 667495085-(4-(4-chlorobenzyl)-2-(pyridin-4-yl)thiazol-5-yl)-1H-pyrazole-3-carboxylic acidYield 7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 5-(4-(4-chlorobenzyl)-2-(pyridin-4-yl)thiazol-5-yl)-1H-pyrazole-3-carboxylate (16.1 mg, 0.0379 mmol) in THF (0.50 mL) was treated with 1.0 M aqueous LiOH (0.0568 mL, 0568 mmol) and the solution was stirred at 40 degrees for 3 days. The reaction was then heated at 65 degrees for 6 hours. The reaction mixture was cooled and acidified with 1N HCl. The solution was extracted with EA (3×25 mL) and the combined organic layers were dried, filtered and concentrated in vacuo. The residue was purified by preparative reverse phase chromatography to give 1 mg (7% yield) of the title compound as a white solid. LC/MS (FA) ES+ 397, 399.

Workup

  1. temperatureThe reaction was then heated at 65 degrees for 6 hours
  2. temperatureThe reaction mixture was cooled
  3. extractionThe solution was extracted with EA (3×25 mL)
  4. customthe combined organic layers were dried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by preparative reverse phase chromatography

Sources & evidence

ORD record
ord-9d35dd489c184fb69d7fdc9f3ac61875
Source dataset
uspto-grants-2014_08
Patent number
US08796268B2

Reaction notes

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