Hydrochloric Acid → N-(2-fluoro-5-hydroxyphenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamide

HRID 1667821

Reaction equation

HRID 1667821 reaction equation
C(=O)(OC)[O:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[C:5]([NH:10][C:11]([C:13]2[N:17]([CH3:18])[N:16]=[C:15]([CH3:19])[CH:14]=2)=[O:12])[CH:4]=1.[OH-].[Na+].Cl>CO>[F:9][C:6]1[CH:7]=[CH:8][C:3]([OH:2])=[CH:4][C:5]=1[NH:10][C:11]([C:13]1[N:17]([CH3:18])[N:16]=[C:15]([CH3:19])[CH:14]=1)=[O:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 575054333-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}-4-fluorophenyl methyl carbonate

Product 1

HCID 57505434N-(2-fluoro-5-hydroxyphenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamideYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}-4-fluorophenyl methyl carbonate (448 mg, 1.46 mmol) in methanol (10 mL) was added 1N aqueous sodium hydroxide solution (2 mL, 2 mmol) under ice-cooling, and the mixture was stirred at room temperature for 40 min. Under ice-cooling, 1N hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtrated. The solvent was evaporated under reduced pressure, and the residue was recrystallized from diethyl ether/hexane to give the title compound (305 mg, 84%) as a white powder.

Workup

  1. temperaturecooling
  2. temperatureUnder ice-cooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltrated
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was recrystallized from diethyl ether/hexane

Sources & evidence

ORD record
ord-a442603633d94c50b59a8e34eb647eb1
Source dataset
uspto-grants-2011_10
Patent number
US08044049B2

Linked notes

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