[2,2-Dimethyl-4-(3-methylamino-4-nitro-benzoyl)-piperazin-1-yl]-(1-phenyl-1H-[1,2,4]-triazol-3-yl)-methanone → [4-(4-Amino-3-methylamino-benzoyl)-2,2-dimethyl-piperazin-1-yl]-(1-phenyl-1H-[1,2,4]-triazol-3-yl)-methanone

HRID 334073Notes

Reaction equation

HRID 334073 reaction equation
[CH3:1][C:2]1([CH3:34])[CH2:7][N:6]([C:8](=[O:20])[C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[C:11]([NH:18][CH3:19])[CH:10]=2)[CH2:5][CH2:4][N:3]1[C:21]([C:23]1[N:27]=[CH:26][N:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:24]=1)=[O:22]>[Ni].CO>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([C:8]([N:6]2[CH2:5][CH2:4][N:3]([C:21]([C:23]3[N:27]=[CH:26][N:25]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[N:24]=3)=[O:22])[C:2]([CH3:34])([CH3:1])[CH2:7]2)=[O:20])=[CH:10][C:11]=1[NH:18][CH3:19]

Participants

4

Reactant 1

HCID 86688294[2,2-Dimethyl-4-(3-methylamino-4-nitro-benzoyl)-piperazin-1-yl]-(1-phenyl-1H-[1,2,4]-triazol-3-yl)-methanone

Product 1

HCID 86688295[4-(4-Amino-3-methylamino-benzoyl)-2,2-dimethyl-piperazin-1-yl]-(1-phenyl-1H-[1,2,4]-triazol-3-yl)-methanone

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 445 mg (0.960 mmol) [2,2-dimethyl-4-(3-methylamino-4-nitro-benzoyl)-piperazin-1-yl]-(1-phenyl-1H-[1,2,4]-triazol-3-yl)-methanone and 300 mg Raney nickel in 50 mL MeOH was hydrogenated at RT for 7.5 h. The catalyst was removed by filtration and the solvent was evaporated in vacuo.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-6a46dd9fca0844d7a179bd96278e9d64
Source dataset
uspto-grants-2014_11
Patent number
US08883789B2

Reaction notes

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