[3,5-Dimethyl-1-(4-nitro-benzyl)-1H-pyrazol-4-yl]-acetic acid methyl ester → [1-(4-aminobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl]acetic acid methyl ester

HRID 1631902Notes

Reaction equation

HRID 1631902 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH2:4][C:5]1[C:6]([CH3:21])=[N:7][N:8]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=2)[C:9]=1[CH3:10]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:22])[CH2:4][C:5]1[C:6]([CH3:21])=[N:7][N:8]([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([NH2:18])=[CH:16][CH:17]=2)[C:9]=1[CH3:10]

Participants

4

Reactant 1

HCID 66707610[3,5-Dimethyl-1-(4-nitro-benzyl)-1H-pyrazol-4-yl]-acetic acid methyl ester2×

Product 1

HCID 66707335[1-(4-aminobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl]acetic acid methyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of [3,5-dimethyl-1-(4-nitro-benzyl)-1H-pyrazol-4-yl]-acetic acid methyl ester (intermediate 1.1.2, 3.90 g, 10.3 mmol) in methanol (10 mL) was added 10% palladium on charcoal (500 mg) and the mixture was hydrogenated. The catalyst was filtered off and the filtrate was concentrated under reduced pressure. The mixture was purified via preparative reversed phase HPLC (gradient of methanol in water+0.1% NH3).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe mixture was purified via preparative reversed phase HPLC (gradient of methanol in water+0.1% NH3)

Sources & evidence

ORD record
ord-d7c7baeff6ca4c009174bf793af0a31e
Source dataset
uspto-grants-2014_07
Patent number
US08791272B2

Reaction notes

Loading…