N-(4-Fluoro-3-chloro-phenyl)-2-(4-fluoro-piperidinyl)-4-methylamino-5-nitro-benzoic acid amide → N-(4-Fluoro-3-chloro-phenyl)-2-(4-fluoro-piperidinyl)-4-methylamino-5-amino-benzoic acid amide

HRID 1189632Notes

Reaction equation

HRID 1189632 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:28])[C:10]2[CH:15]=[C:14]([N+:16]([O-])=O)[C:13]([NH:19][CH3:20])=[CH:12][C:11]=2[N:21]2[CH2:26][CH2:25][CH:24]([F:27])[CH2:23][CH2:22]2)=[CH:4][C:3]=1[Cl:29]>[Ni].C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:28])[C:10]2[CH:15]=[C:14]([NH2:16])[C:13]([NH:19][CH3:20])=[CH:12][C:11]=2[N:21]2[CH2:26][CH2:25][CH:24]([F:27])[CH2:23][CH2:22]2)=[CH:4][C:3]=1[Cl:29]

Participants

4

Reactant 1

HCID 67957338N-(4-Fluoro-3-chloro-phenyl)-2-(4-fluoro-piperidinyl)-4-methylamino-5-nitro-benzoic acid amide

Product 1

HCID 67957421N-(4-Fluoro-3-chloro-phenyl)-2-(4-fluoro-piperidinyl)-4-methylamino-5-amino-benzoic acid amide

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N-(4-fluoro-3-chloro-phenyl)-2-(4-fluoro-piperidinyl)-4-methylamino-5-nitro-benzoic acid amide (90 mg, 0.21 mmol), Ra—Ni (30 mg) and THF (10 mL) is stirred under 50 psi H2-atmosphere for 4 h. The mixture is filtered, and the filtrate is concentrated.

Workup

  1. filtrationThe mixture is filtered
  2. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-58c747ad0ed148e78695a39575a8a2ed
Source dataset
uspto-grants-2014_03
Patent number
US08674113B2

Reaction notes

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