3-(1-cyano-1-methylethyl)-N-{4-ethyl-3-[(5-nitropyridin-2-yl)oxy]phenyl}benzamide → N-{3-[(5-aminopyridin-2-yl)oxy]-4-ethylphenyl}-3-(1-cyano-1-methylethyl)benzamide

HRID 1800471Notes

Reaction equation

HRID 1800471 reaction equation
[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:30]=[CH:31][CH:32]=1)[C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH3:19])=[C:14]([O:20][C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][N:22]=2)[CH:13]=1)=[O:10])([CH3:5])[CH3:4])#[N:2]>CO.[C].[Pd]>[NH2:27][C:24]1[CH:25]=[CH:26][C:21]([O:20][C:14]2[CH:13]=[C:12]([NH:11][C:9](=[O:10])[C:8]3[CH:30]=[CH:31][CH:32]=[C:6]([C:3]([C:1]#[N:2])([CH3:5])[CH3:4])[CH:7]=3)[CH:17]=[CH:16][C:15]=2[CH2:18][CH3:19])=[N:22][CH:23]=1

Participants

4

Reactant 1

HCID 684201193-(1-cyano-1-methylethyl)-N-{4-ethyl-3-[(5-nitropyridin-2-yl)oxy]phenyl}benzamide

Product 1

HCID 68417667N-{3-[(5-aminopyridin-2-yl)oxy]-4-ethylphenyl}-3-(1-cyano-1-methylethyl)benzamideYield 84%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-(1-cyano-1-methylethyl)-N-{4-ethyl-3-[(5-nitropyridin-2-yl)oxy]phenyl}benzamide (2.78 g, 6.48 mmol) in methanol (70 mL) was added 10% palladium-carbon powder (640 mg), and the mixture was stirred at room temperature for 5 hr under a hydrogen atmosphere of 3.0 pressure. Palladium-carbon powder was filtered off by celite filtration, the filtrate was concentrated under reduced pressure, and the obtained residue was washed with ethyl acetate/tetrahydrofuran (10:1) to give the title compound (2.18 g, 84%) as a gray powder.

Workup

  1. filtrationPalladium-carbon powder was filtered off by celite filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. washthe obtained residue was washed with ethyl acetate/tetrahydrofuran (10:1)

Sources & evidence

ORD record
ord-23f1b25b208042ca8b88af8dd70a26e7
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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