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 133612Notes

Reaction equation

HRID 133612 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]>[C].[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 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A mixture of the resulting 4-[[N-(2-amino-4,5-difluorobenzoyl)glycyl]aminomethyl]-1-(4-methyl-3-nitrobenzyl)piperidine with a 5% palladium carbon (15 mg) and methanol (2 mL) was stirred at room temperature under a hydrogen atmosphere for 4 hours. The palladium catalyst was removed by filtration through Celite, and the filtrate was concentrated and purified by preparative TLC (SiO2, ethyl acetate/methanol=3:1) to thereby provide 4-[[N-(2-amino-4,5-difluorobenzoyl)glycyl]aminomethyl]-1-(3-amino-4-methylbenzyl)piperidine (Compd. 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. customThe palladium catalyst was removed by filtration through Celite
  2. concentrationthe filtrate was concentrated
  3. custompurified by preparative TLC (SiO2, ethyl acetate/methanol=3:1) to thereby provide 4-[[N-(2-amino-4,5-difluorobenzoyl)glycyl]aminomethyl]-1-(3-amino-4-methylbenzyl)piperidine (Compd. No

Sources & evidence

ORD record
ord-f7d7116733fc49d9ab2ae21a43b7fcbf
Source dataset
uspto-grants-2008_06
Patent number
US07390830B1

Reaction notes

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