Hydrogen chloride-ethyl acetate → HCID 68411870, compound

HRID 2194737Notes

Reaction equation

HRID 2194737 reaction equation
[CH3:1][N:2]([CH2:10][C:11]1[CH:15]=[C:14]([N:16]([CH3:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:13]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:12]=1)C(=O)OC(C)(C)C.C(OCC)(=O)C.[ClH:36]>C(OCC)(=O)C.CO>[ClH:36].[CH3:23][N:16]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:14]1[N:13]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:12]=[C:11]([CH2:10][NH:2][CH3:1])[CH:15]=1

Participants

5

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 68408884HCID 68408884, compound

Product 1

HCID 68411870HCID 68411870, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl methyl({5-[methyl(phenyl)amino]-1-phenyl-1H-pyrazol-3-yl}methyl)carbamate (67 mg) was dissolved in ethyl acetate (1 mL) and methanol (0.5 mL), a 4 mol/L hydrogen chloride-ethyl acetate solution (2 mL) was added, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, and the residue was crystallized from a mixed solvent of ethyl acetate and hexane, and recrystallized from a mixed solvent of ethyl acetate and ethanol to give the title compound as colorless crystals (yield 25 mg, yield 45%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was crystallized from a mixed solvent of ethyl acetate and hexane
  3. customrecrystallized from a mixed solvent of ethyl acetate and ethanol

Sources & evidence

ORD record
ord-3faeb6670a454eecb062259ab81b8b03
Source dataset
uspto-grants-2012_12
Patent number
US08334301B2

Reaction notes

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