N-(4-(Methylamino)-3-nitrobenzoyl)-N-2-pyridinyl-beta-alanine ethyl ester → N-(3-Amino-4-(methylamino)benzoyl)-N-2-pyridinyl-beta-alanine ethyl ester

HRID 919279Notes

Reaction equation

HRID 919279 reaction equation
[CH3:1][NH:2][C:3]1[CH:24]=[CH:23][C:6]([C:7]([N:9]([CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[O:8])=[CH:5][C:4]=1[N+:25]([O-])=O>ClCCl.CO.[Pd]>[NH2:25][C:4]1[CH:5]=[C:6]([CH:23]=[CH:24][C:3]=1[NH:2][CH3:1])[C:7]([N:9]([CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)=[O:8]

Participants

5

Reactant 1

HCID 11079230N-(4-(Methylamino)-3-nitrobenzoyl)-N-2-pyridinyl-beta-alanine ethyl ester

Product 1

HCID 11982993N-(3-Amino-4-(methylamino)benzoyl)-N-2-pyridinyl-beta-alanine ethyl ester

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

The process disclosed in WO 98/37075 also involves the reduction of ethyl 3-(4-(methylamino)-3-nitro-N-(pyridin-2-yl)benzamido)propanoate (herein after referred as “nitro compound”) using Pd—C in a mixture of dichloromethane and methanol under hydrogen pressure to provide ethyl 3-(3-amino-4-(methylamino)-N-(pyridin-2-yl)benzamido)propanoate (herein after referred as “diamine compound”).

Sources & evidence

ORD record
ord-22e8c03533bd402a90929a8e6f8b081e
Source dataset
uspto-grants-2016_03
Patent number
US09273030B2

Reaction notes

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