4-[[N-(2-amino-4,5-difluorobenzoyl)glycyl]aminomethyl]-1-(4-methyl-3-nitrobenzyl)piperidine → 4-[[N-(2-amino-4,5-difluorobenzoyl)glycyl]aminomethyl]-1-(3-amino-4-methylbenzyl)piperidine

HRID 279328Notes

Reaction equation

HRID 279328 reaction equation
[NH2:1][C:2]1[CH:32]=[C:31]([F:33])[C:30]([F:34])=[CH:29][C:3]=1[C:4]([NH:6][CH2:7][C:8]([NH:10][CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[C:21]([N+:26]([O-])=O)[CH:20]=2)[CH2:14][CH2:13]1)=[O:9])=[O:5]>[Pd].CO>[NH2:1][C:2]1[CH:32]=[C:31]([F:33])[C:30]([F:34])=[CH:29][C:3]=1[C:4]([NH:6][CH2:7][C:8]([NH:10][CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[C:21]([NH2:26])[CH:20]=2)[CH2:14][CH2:13]1)=[O:9])=[O:5]

Participants

4

Reactant 1

HCID 184262824-[[N-(2-amino-4,5-difluorobenzoyl)glycyl]aminomethyl]-1-(4-methyl-3-nitrobenzyl)piperidine

Product 1

HCID 184261324-[[N-(2-amino-4,5-difluorobenzoyl)glycyl]aminomethyl]-1-(3-amino-4-methylbenzyl)piperidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-[{N-(2-amino-4,5-difluorobenzoyl)glycyl}aminomethyl]-1-(4-methyl-3-nitrobenzyl)piperidine prepared above, 5% palladium-activated carbon (15 mg), and methanol (2 mL) was stirred under a hydrogen atmosphere at room temperature for 4 h. The Pd catalyst was filtered off through Celite and the filtrate was concentrated. Preparative TLC (SiO2, ethyl acetate/MeOH=3/1) gave 4-[{N-(2-amino-4, 5-difluorobenzoyl)glycyl}aminomethyl]-1-(3-amino-4-methylbenzyl)piperidine (Compound No. 2114) (2.9 mg, 13%): The purity was determined by RPLC/MS (100%); ESI/MS m/e 446.1 (M++H, C23H29F2N5O2).

Workup

  1. filtrationThe Pd catalyst was filtered off through Celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-4d486a03dc3749489245fa3eadc859e3
Source dataset
uspto-grants-2002_03
Patent number
US06362177B1

Reaction notes

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