Hydrogen chloride-ethyl acetate → HCID 68409985, compound

HRID 2194738Notes

Reaction equation

HRID 2194738 reaction equation
C(O[C:6](=O)[N:7]([CH2:9][C:10]1[CH:14]=[C:13]([N:15]([C:22](=[O:24])[CH3:23])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:12]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:11]=1)C)(C)(C)C.C(OCC)(=O)C.Cl>C(OCC)(=O)C.C(O)C>[CH3:6][NH:7][CH2:9][C:10]1[CH:14]=[C:13]([N:15]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:22](=[O:24])[CH3:23])[N:12]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:11]=1

Participants

5

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 68478407HCID 68478407, compound

Product 1

HCID 68409985HCID 68409985, compoundYield 50.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl({5-[acetyl(phenyl)amino]-1-phenyl-1H-pyrazol-3-yl}methyl)methylcarbamate (83 mg) was dissolved in ethyl acetate (2 mL) and ethanol (1 mL), a 4 mol/L hydrogen chloride-ethyl acetate solution (3 mL) was added, and the mixture was stirred at room temperature for 3 hr. The reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate solution was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was dissolved in ethyl acetate (3 mL), and the mixture was added to a solution of fumaric acid (23 mg) in ethanol (5 mL). The solvent was evaporated under reduced pressure, and the residue was recrystallized from a mixed solvent of ethyl acetate and ethanol to give the title compound as colorless crystals (yield 32 mg, yield 43%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate solution
  2. additionwas added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue was dissolved in ethyl acetate (3 mL)
  8. additionthe mixture was added to a solution of fumaric acid (23 mg) in ethanol (5 mL)
  9. customThe solvent was evaporated under reduced pressure
  10. customthe residue was recrystallized from a mixed solvent of ethyl acetate and ethanol

Sources & evidence

ORD record
ord-81866b4154784e98be229d58ea7d80f5
Source dataset
uspto-grants-2012_12
Patent number
US08334301B2

Reaction notes

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