Ammonium formate → HCID 11225063, compound

HRID 2252074Notes

Reaction equation

HRID 2252074 reaction equation
[CH:1]([S:4]([N:7]1[C:11]2[CH:12]=[C:13]([C:16]3[N:17]=[C:18]([CH:27]4[CH2:32][CH2:31][N:30](C(OCC5C=CC=CC=5)=O)[CH2:29][CH2:28]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[NH2:43])(=[O:6])=[O:5])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>[Pd].C(O)C>[CH:1]([S:4]([N:7]1[C:11]2[CH:12]=[C:13]([C:16]3[N:17]=[C:18]([CH:27]4[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]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[NH2:43])(=[O:5])=[O:6])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 17981625HCID 17981625, compound

Product 1

HCID 11225063HCID 11225063, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Vigorously stir a mixture of 1-isopropylsulfonyl-2-amino-6-(2-(1-(benzyloxycarbonyl)piperidin-4-yl)-5-(phenyl)-imidazol-4-yl)-benzimidazole (0.74 g, 1.24 mmol), ammonium formate (4.94 mmol), and 10% palladium on carbon (0.12 mmol) in 30 mL absolute ethanol at reflux for 5 hours. Cool the reaction mixture to room temperature, filter through a bed of Celite®, and concentrate the filtrate under reduced pressure. Subject the residue to silica gel chromatography, eluting with 19:1 dichloromethane:methanol to provide the title compound. MS(ES+): m/z=465.2 (M+H)+

Workup

  1. temperatureat reflux for 5 hours
  2. filtrationfilter through a bed of Celite®
  3. concentrationconcentrate the filtrate under reduced pressure
  4. washeluting with 19:1 dichloromethane

Sources & evidence

ORD record
ord-d9e8a8afebe94f228dd3e82ef7c2ec13
Source dataset
uspto-grants-2008_01
Patent number
US07320995B2

Reaction notes

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