5-Aminobenzimidazole → HCID 178424603, compound

HRID 706269Notes

Reaction equation

HRID 706269 reaction equation
Cl[C:2](OC1C=CC([N+]([O-])=O)=CC=1)=[O:3].[NH2:14][C:15]1[CH:23]=[CH:22][C:18]2[N:19]=[CH:20][NH:21][C:17]=2[CH:16]=1.[NH2:24][CH2:25][C:26]([C:28]1[CH:33]=[CH:32][C:31](Cl)=[C:30]([CH3:35])[CH:29]=1)=O>C(Cl)Cl>[NH:19]1[C:18]2[CH:22]=[CH:23][C:15]([N:14]3[CH:26]([C:28]4[CH:29]=[C:30]([CH3:35])[CH:31]=[CH:32][CH:33]=4)[CH2:25][NH:24][C:2]3=[O:3])=[CH:16][C:17]=2[N:21]=[CH:20]1

Participants

5

Reactant 3

HCID 136235-AminobenzimidazoleHCID 821294-Nitrophenyl chloroformateHCID 67035926HCID 67035926, compound

Product 1

HCID 178424603HCID 178424603, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The compound was synthesized as hydrochloride salt by the following procedure. 4-Nitrophenyl chloroformate (0.564 g, 3.5 mmol) was dissolved CH2Cl2, cooled down to 0° C. and 5-aminobenzimidazole (0.466 g, 3.5 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 The mixture was stirred at ambient temperature for 2 h. The resulted solid was withdrawn by suction, dried and taken up in a small amount of DMF. To the solution aminomethyl-(4-chloro-3-methylphenyl)ketone (0.774, 3.5 mmol) and TEA (1.46 ml, 10.5 mmol) was 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 solvent was removed and purified by means of preparative HPLC.

Workup

  1. customto adapt ambient temperature
  2. customThe resulted solid was withdrawn by suction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. customthe solvent was removed
  12. custompurified by means of preparative HPLC

Sources & evidence

ORD record
ord-0cf8839902024e5aa083606546018a15
Source dataset
uspto-grants-2015_11
Patent number
US09173885B2

Reaction notes

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