Hydrochloric Acid → HCID 90184716, compound

HRID 1750393Notes

Reaction equation

HRID 1750393 reaction equation
C([O:4][CH2:5][C:6]([N:9]1[C:13]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[C:12]([C:21](=[O:23])[NH2:22])[CH:11]=[N:10]1)([CH3:8])[CH3:7])(=O)C.[OH-].[Na+].O.Cl>CO>[F:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]2[N:9]([C:6]([CH3:8])([CH3:7])[CH2:5][OH:4])[N:10]=[CH:11][C:12]=2[C:21]([NH2:22])=[O:23])=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 90184505HCID 90184505, compound

Product 1

HCID 90184716HCID 90184716, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of the compound (95 mg, 0.30 mmol) obtained in step 1 in methanol (3 mL) was added 6N aqueous sodium hydroxide solution (0.05 mL), and the mixture was stirred at 60° C. for 1 hr. To the reaction mixture were added water and 6M hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried, and the solvent was evaporated under reduced pressure to give 5-(4-fluorophenyl)-1-(1-hydroxy-2-methylpropan-2-yl)-1H-pyrazole-4-carboxamide (60 mg, 0.216 mmol, 73%) as a white powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b6fffbbad91b4ea1a4d565df2f8e0a24
Source dataset
uspto-grants-2015_10
Patent number
US09156837B2

Reaction notes

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