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

HRID 1800490Notes

Reaction equation

HRID 1800490 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]([C:18]#[N: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[C:18]#[N:19])=[N:22][CH:23]=1

Participants

4

Reactant 1

HCID 684179083-(1-cyano-1-methylethyl)-N-{4-cyano-3-[(5-nitropyridin-2-yl)oxy]phenyl}benzamide

Product 1

HCID 68418578N-{3-[(5-aminopyridin-2-yl)oxy]-4-cyanophenyl}-3-(1-cyano-1-methylethyl)benzamideYield 90.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-(1-cyano-1-methylethyl)-N-{4-cyano-3-[(5-nitropyridin-2-yl)oxy]phenyl}benzamide (0.65 g, 1.59 mmol) in methanol (20 mL) was added 10% palladium-carbon (130 mg), and the mixture was stirred at room temperature for 20 hr under a hydrogen atmosphere (2.8 atm). The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound (0.57 g, 90%) as a pale-yellow oil. This was used for the next reaction without further purification.

Workup

  1. filtrationThe insoluble material was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b3d1a42008d94805b3ea5f5b8f5f5d6d
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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