2-(3-isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazole-5-carbonitrile → 1-[5-aminomethyl-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-3-isopropyl-1,3-dihydro-benzoimidazol-2-one

Participants

Reaction Steps

A mixture of 2-(3-isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazole-5-carbonitrile (230 mg, 0.57 mmol) and 10% palladium on carbon (50 mg) in 5% HCl-MeOH (10 mL) was placed in a Parr shaker under hydrogen (40 psi) for 6 h. The reaction mixture was filtered through celite and the solvent evaporated. The residue was purified by prep-HPLC (gradient 10% -100% B) to give 148 mg (64%) of 1-[5-aminomethyl-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-3-isopropyl-1,3-dihydro-benzoimidazol-2-one as a hygroscopic white solid.

Provenance & Evidence