Hydrochloric Acid → 1-(4-Methoxyphenyl)-1H-pyrazol-3-amine

HRID 610148Notes

Reaction equation

HRID 610148 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:13]=[CH:12][C:11]([NH:14]C(OC)=O)=[N:10]2)=[CH:5][CH:4]=1.[OH-].[K+].Cl>O.CO.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH:13]=[CH:12][C:11]([NH2:14])=[N:10]2)=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 543443991-[(4-Methoxy)phenyl]-3-[(methoxycarbonyl)amino]-1H-pyrazole

Product 1

HCID 167406551-(4-Methoxyphenyl)-1H-pyrazol-3-amineYield 94.4%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
70 °C

Procedure

To a solution of 1-[(4-methoxy)phenyl]-3-[(methoxycarbonyl)amino]-1H-pyrazole-5-[(2'-aminosulfonyl-[1,1']-biphen-4-yl)carboxyamide (0.22 g, 0.42 mmol) in 10 mL of 1:1 water/methanol was added potassium hydroxide (2.0 g, 35 mmol). The resulting mixture was stirred at 70° C. for 4 h and then was cooled to ambient temperature and was acidified with aq HCl. The reaction mixture was diluted with ethyl acetate and the organics were washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by prep HPLC (C18 reverse phase column, elution with a H2O/CH3CN gradient with 0.5% TFA) and lyophilized to afford 75 mg (38%) of the title compound as a white powder. LRMS (ES+): 463.8 (M+H)+.

Workup

  1. temperaturewas cooled to ambient temperature
  2. washthe organics were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by prep HPLC (
  6. washC18 reverse phase column, elution with a H2O/CH3CN gradient with 0.5% TFA) and

Sources & evidence

ORD record
ord-7599911cb28646da8050b449413c4a86
Source dataset
uspto-grants-1999_12
Patent number
US05998424

Reaction notes

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