HCID 17981721, compound → HCID 17981722, compound

HRID 2252073Notes

Reaction equation

HRID 2252073 reaction equation
[CH:1]([S:4]([N:7]1[C:11]2[CH:12]=[C:13]([C:16]3[N:17]=[C:18]([C:27]4[CH:32]=[CH:31][C:30]([N+:33]([O-])=O)=[CH:29][CH:28]=4)[NH:19][C:20]=3[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[NH2:36])(=[O:6])=[O:5])([CH3:3])[CH3:2].[H][H]>[Pd].CO>[CH:1]([S:4]([N:7]1[C:11]2[CH:12]=[C:13]([C:16]3[N:17]=[C:18]([C:27]4[CH:28]=[CH:29][C:30]([NH2:33])=[CH:31][CH:32]=4)[NH:19][C:20]=3[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[NH2:36])(=[O:5])=[O:6])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 17981721HCID 17981721, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 17981722HCID 17981722, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Purge a suspension of 1-isopropylsulfonyl-2-amino-6-(2-(4-nitrophenyl)-5-(phenyl)-imidazol-4-yl)-benzimidazole (0.149 g, 0.3 mmol) and 10% palladium on carbon (0.03 mmol) in methanol with hydrogen for 10 minutes and then stir under a hydrogen atmosphere for 6 hours. Filter through a bed of Celite® and concentrate the residue under reduced pressure. Subject the residue to silica gel chromatography, eluting with 4% methanol in dichloromethane to provide the title compound in 28% yield. MS(ES+): m/z=473.0 (M+H)+

Workup

  1. customPurge
  2. filtrationFilter through a bed of Celite®
  3. concentrationconcentrate the residue under reduced pressure
  4. washeluting with 4% methanol in dichloromethane

Sources & evidence

ORD record
ord-1e0498dd4de74bd1a9fd035a891daee4
Source dataset
uspto-grants-2008_01
Patent number
US07320995B2

Reaction notes

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