2-(5-cyclobutoxy-2-nitrophenyl)-N-(3-(trifluoromethyl)benzyl)isonicotinamide → 2-(2-amino-5-cyclobutoxyphenyl)-N-(3-(trifluoromethyl)benzyl)isonicotinamide

HRID 625322Notes

Reaction equation

HRID 625322 reaction equation
[CH:1]1([O:5][C:6]2[CH:7]=[CH:8][C:9]([N+:32]([O-])=O)=[C:10]([C:12]3[CH:13]=[C:14]([CH:29]=[CH:30][N:31]=3)[C:15]([NH:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=3)=[O:16])[CH:11]=2)[CH2:4][CH2:3][CH2:2]1>[Pd].CO>[NH2:32][C:9]1[CH:8]=[CH:7][C:6]([O:5][CH:1]2[CH2:2][CH2:3][CH2:4]2)=[CH:11][C:10]=1[C:12]1[CH:13]=[C:14]([CH:29]=[CH:30][N:31]=1)[C:15]([NH:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:26])([F:27])[F:28])[CH:20]=1)=[O:16]

Participants

4

Reactant 1

HCID 665876992-(5-cyclobutoxy-2-nitrophenyl)-N-(3-(trifluoromethyl)benzyl)isonicotinamide

Product 1

HCID 665867962-(2-amino-5-cyclobutoxyphenyl)-N-(3-(trifluoromethyl)benzyl)isonicotinamideYield 79.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 62 mg of 2-(5-cyclobutoxy-2-nitrophenyl)-N-(3-(trifluoromethyl)benzyl)isonicotinamide, 10 mg of 10% Pd/C, and 4 mL of methanol was stirred for 2 h under a hydrogen atmosphere. The mixture was filtered and concentrated to give 46 mg of product.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-27062a81c13345cc8ca056c194b2ad83
Source dataset
uspto-grants-2016_04
Patent number
US09301951B2

Reaction notes

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