1,3-dimethyl-N-{2-methyl-5-[(6-nitropyridin-3-yl)oxy]phenyl}-1H-pyrazole-5-carboxamide → N-{5-[(6-aminopyridin-3-yl)oxy]-2-methylphenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide

HRID 1874332

Reaction equation

HRID 1874332 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([NH:9][C:10]2[CH:15]=[C:14]([O:16][C:17]3[CH:18]=[N:19][C:20]([N+:23]([O-])=O)=[CH:21][CH:22]=3)[CH:13]=[CH:12][C:11]=2[CH3:26])=[O:8])=[CH:5][C:4]([CH3:27])=[N:3]1>CO.[C].[Pd]>[NH2:23][C:20]1[N:19]=[CH:18][C:17]([O:16][C:14]2[CH:13]=[CH:12][C:11]([CH3:26])=[C:10]([NH:9][C:7]([C:6]3[N:2]([CH3:1])[N:3]=[C:4]([CH3:27])[CH:5]=3)=[O:8])[CH:15]=2)=[CH:22][CH:21]=1

Participants

4

Reactant 1

HCID 577493301,3-dimethyl-N-{2-methyl-5-[(6-nitropyridin-3-yl)oxy]phenyl}-1H-pyrazole-5-carboxamide

Product 1

HCID 57749384N-{5-[(6-aminopyridin-3-yl)oxy]-2-methylphenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamideYield 95%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1,3-dimethyl-N-{2-methyl-5-[(6-nitropyridin-3-yl)oxy]phenyl}-1H-pyrazole-5-carboxamide (3.38 g, 9.20 mmol) in methanol (20 mL) was added palladium carbon (50% water-containing product, 300 mg), and the mixture was stirred under a hydrogen atmosphere at room temperature for 4 hr. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was collected by filtration and washed with ethyl acetate-hexane to give the title compound (2.94 g, 95%) as a white solid.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. filtrationThe residue was collected by filtration
  4. washwashed with ethyl acetate-hexane

Sources & evidence

ORD record
ord-483ad65a89a841d0961d5d17a785dd2b
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Linked notes

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