5-Aminobenzimidazole → HCID 178441338, compound

HRID 706266Notes

Reaction equation

HRID 706266 reaction equation
Cl[C:2](OC1C=CC=CC=1)=[O:3].[NH2:11][C:12]1[CH:20]=[CH:19][C:15]2[N:16]=[CH:17][NH:18][C:14]=2[CH:13]=1.[NH2:21][CH2:22][C:23](=O)[C:24]([CH3:27])([CH3:26])[CH3:25]>C(Cl)Cl>[C:24]([CH:23]1[N:11]([C:12]2[CH:20]=[CH:19][C:15]3[NH:16][CH:17]=[N:18][C:14]=3[CH:13]=2)[C:2](=[O:3])[NH:21][CH2:22]1)([CH3:27])([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 136235-AminobenzimidazoleHCID 15891Phenyl chloroformateHCID 4266281-Amino-3,3-dimethylbutan-2-one

Product 1

HCID 178441338HCID 178441338, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The compound was synthesized as hydrochloride salt by the following procedure. Phenyl chloroformate (0.98 mL, 7.8 mmol) was dissolved in CH2Cl2, cooled down to 0° C. and 5-aminobenzimidazole (0.865 g, 6.5 mmol) was added slowly. The mixture was kept at 0° C. for 30 min and then the mixture was allowed to adapt ambient temperature. The mixture was stirred at ambient temperature for 2 h. The resulting solid was withdrawn by suction, dried and taken up in a small amount of DMF. To the solution, 1-amino-3,3-dimethylbutan-2-one (0.986, 6.5 mmol) and TEA (2.73 mL, 19.5 mmol) were added. The mixture was kept at 40° C. for 2 h. The solvent was removed and purified by means of preparative HPLC. The remains were re-dissolved in MeOH and a small amount of HCl was added (1-2%). The solution was subjected to hydrogenation (PdC, 10% on charcoal, 4 bar, 60° C.) for 4 h. The catalyst was removed by filtration through a pad of CELITE® and the residue was washed with water. The organic layer was dried, filtrated and the solvent was removed to result in the final product.

Workup

  1. customto adapt ambient temperature
  2. customThe resulting solid was withdrawn by suction
  3. customdried
  4. waitThe mixture was kept at 40° C. for 2 h
  5. customThe solvent was removed
  6. custompurified by means of preparative HPLC
  7. dissolutionThe remains were re-dissolved in MeOH
  8. additiona small amount of HCl was added (1-2%)
  9. waitThe solution was subjected to hydrogenation (PdC, 10% on charcoal, 4 bar, 60° C.) for 4 h
  10. customThe catalyst was removed by filtration through a pad of CELITE®
  11. washthe residue was washed with water
  12. customThe organic layer was dried
  13. filtrationfiltrated
  14. customthe solvent was removed

Sources & evidence

ORD record
ord-e2d64cf0ca5e4ed5b703cc3244a8359f
Source dataset
uspto-grants-2015_11
Patent number
US09173885B2

Reaction notes

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