Hydrochloric Acid → HCID 66587674, compound

HRID 1630683Notes

Reaction equation

HRID 1630683 reaction equation
[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]([O:15]C)=[O:14])=[CH:11][C:10]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][N:19]=3)=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[OH-].[Na+].Cl>C(O)C.O>[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:25])[F:26])=[CH:20][N:19]=3)=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66587467HCID 66587467, compound

Product 1

HCID 66587674HCID 66587674, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

855 mg (2.15 mmol) of methyl 1-(3-chloropyridin-2-yl)-3-{[5-(trifluoromethyl)pyridin-2-yl]amino}-1H-pyrazole-5-carboxylate were dissolved in 10.0 ml of ethanol, and 248 mg (2.79 mmol) of 45% strength aqueous sodium hydroxide solution were added. After 24 hours of stirring at room temperature, the mixture was diluted with water and acidified with dilute hydrochloric acid. The aqueous phase was extracted repeatedly with ethyl acetate and dried over magnesium sulphate. The solvent was distilled off under reduced pressure, which gave 758 mg (92% of theory) of 1-(3-chloropyridin-2-yl)-3-{[5-(trifluoromethyl)pyridin-2-yl]amino}-1H-pyrazole-5-carboxylic acid. (logP: 2.79; MH+: 384.0; 1H-NMR (400 MHz, CD3CN, δ, ppm): 7.28 (m, 1H), 7.38 (m, 1H), 7.55 (m, 1H), 7.89 (m, 1H), 8.05 (m, 1H), 8.51 (m, 2H).

Workup

  1. extractionThe aqueous phase was extracted repeatedly with ethyl acetate
  2. dry with materialdried over magnesium sulphate
  3. distillationThe solvent was distilled off under reduced pressure, which

Sources & evidence

ORD record
ord-6fd825bbb7f542a68c698dbf66324325
Source dataset
uspto-grants-2014_07
Patent number
US08791139B2

Reaction notes

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