HCID 178418361, compound → HCID 178427151, compound

HRID 2053922Notes

Reaction equation

HRID 2053922 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[C:25]([N:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1)=[O:26])[C:5]([NH:7][C@H:8]([C:10]1[NH:14][C:13]2[CH:15]=[CH:16][C:17]([N+:19]([O-])=O)=[CH:18][C:12]=2[N:11]=1)[CH3:9])=[O:6].[H][H]>CO.[Pd]>[CH3:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[C:25]([N:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1)=[O:26])[C:5]([NH:7][C@H:8]([C:10]1[NH:14][C:13]2[CH:15]=[CH:16][C:17]([NH2:19])=[CH:18][C:12]=2[N:11]=1)[CH3:9])=[O:6]

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178427152HCID 178427152, compound

Product 1

HCID 178427151HCID 178427151, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

40 mg of 3-methyl-N-[(1S)-1-(5-nitro-1H-benzimidazol-2-yl)ethyl]-4-(pyrrolidin-1-ylcarbonyl)benzamide if dissolved in 40 mL of methanol, combined with 10 mg of palladium on activated charcoal (10%), and hydrogenated for 3 hours with hydrogen (3 bar). Then the catalyst is filtered off and the solvent is distilled off. Yield: 83%; Rf value: 0.50 (silica gel; dichloromethane/ethanol=4:1); C22H25N5O2 (391.47); mass spectrum: (M+H)+=392 and (M−H)−=390

Workup

  1. filtrationThen the catalyst is filtered off
  2. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-40e19451f165462987e8bd7d3865213a
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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