Water → HCID 10024171, compound

Participants

Reaction Steps

To a solution of said N-{2-[isopropyl(methyl)amino]-6-nitro-1H-benzimidazole (1.00 g) as obtained in Example 1-(1) in methanol (30 ml), 20% palladium hydroxide-carbon (200 mg) was added and stirred at room temperature under atmospheric pressure for 5 hours. The reaction solution was filtered through Celite, and the filtrate was condensed under reduced pressure. Thus obtained 6-amino-N-{2-isopropyl(methyl)amino]-1H-benzimidazole was dissolved in chloroform (15 ml), followed by successive addition of triethylamine (1.8 ml) and 3-[4-(trifluoromethyl)phenyl]propionic acid (930 mg) and dropwise addition, under cooling with ice, of 2-chloro-1,3-dimethyl-2-imidazolinium chloride (2M chloroform solution, 2.6 ml). After 15 hours' stirring at room temperature, water was added, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The organic layer was condensed under reduced pressure, the resultant residue was purified on silica gel column chromatography, (methanol/ethyl acetate=1/10) and washed with ether to provide the title compound (1.00 g).

Provenance & Evidence