1-[(4-Methoxy)phenyl]-3-[E-2-(methoxycarbonyl)ethenyl]-1H-pyrazole → 1-[(4-Methoxy)phenyl]-3-[2-(methoxycarbonyl)ethyl]-1H-pyrazole

HRID 610154Notes

Reaction equation

HRID 610154 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:13]=[CH:12][C:11](/[CH:14]=[CH:15]/[C:16]([O:18][CH3:19])=[O:17])=[N:10]2)=[CH:5][CH:4]=1.[H][H]>C(O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])=[N:10]2)=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 865879821-[(4-Methoxy)phenyl]-3-[E-2-(methoxycarbonyl)ethenyl]-1H-pyrazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 867549121-[(4-Methoxy)phenyl]-3-[2-(methoxycarbonyl)ethyl]-1H-pyrazoleYield 88.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1-[(4-methoxy)phenyl]-3-[E-2-(methoxycarbonyl) ethenyl]-1H-pyrazole-5-[(2'-aminosulfonyl-[1,1']-biphen-4-yl) carboxyamide (35 mg, 0.065 mmol) in 20 mL of absolute ethanol at ambient temperature was added 10% palladium on carbon catalyst (3.5 mg). This mixture was stirred under 1 atm of hydrogen gas for 3 h and then was filtered through a pad of celite 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 15 mg (42%) of the title compound as a white powder. LRMS (ES+): 534.9 (M+H)+.

Workup

  1. filtrationwas filtered through a pad of celite
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by prep HPLC (
  4. washC18 reverse phase column, elution with a H2O/CH3CN gradient with 0.5% TFA) and

Sources & evidence

ORD record
ord-01fabb2662ee4e44ae3e3f3a428108c7
Source dataset
uspto-grants-1999_12
Patent number
US05998424

Reaction notes

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