Ammonium formate → 1472803-03-4

HRID 2284669Notes

Reaction equation

HRID 2284669 reaction equation
C([O-])=O.[NH4+].[N+:5]([C:8]1[CH:9]=[CH:10][C:11]2[N:15]=[C:14]([CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[NH:13][C:12]=2[CH:25]=1)([O-])=O>CO.[C].[Pd]>[NH2:5][C:8]1[CH:9]=[CH:10][C:11]2[N:15]=[C:14]([CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:21])([CH3:23])[CH3:22])[NH:13][C:12]=2[CH:25]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 90052209HCID 90052209, compound

Product 1

HCID 900524751472803-03-4Yield 105.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To 10% palladium-carbon (50 mg) and ammonium formate (228 mg), a solution of tert-butyl ((6-nitro-1H-benzo[d]imidazol-2-yl)methyl)carbamate (C19, 106 mg) in methanol (4 mL) was added at room temperature, and the mixture was stirred at room temperature for 1 hour and 30 minutes. The insoluble matter was removed by filtration through Cerite, and then the solvent was evaporated under reduced pressure. To the obtained residue, ethyl acetate and water were added. The organic layer was separated, washed with saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain tert-butyl ((6-amino-1H-benzo[d]imidazol-2-yl)methyl)carbamate (C20, 100 mg).

Workup

  1. customThe insoluble matter was removed by filtration through Cerite
  2. customthe solvent was evaporated under reduced pressure
  3. additionTo the obtained residue, ethyl acetate and water were added
  4. customThe organic layer was separated
  5. washwashed with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-4ae63e2257b14f9aae358254bca21732
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

Loading…