Diisopropylethylamine → 1-{2-[(4-Hydroxypiperidine-1-carbonyl)-amino]-ethyl}-1H-benzoimidazole-5-carboxylic Acid (5-hydroxy-adamantan-2-yl)-amide

Participants

Reaction Steps

To a solution of 1-(2-aminoethyl)-1H-benzimidazole-5-carboxylic acid (5-hydroxy-adamantan-2-yl)-amide (0.35 g, 0.988 mmol) in dry THF (5 mL) was added DIPEA (0.3 mL, 1.91 mmol) at 0° C. To this reaction mixture was added 4-hydroxypiperidine-1-carbonyl chloride slowly and stirred for 2 h at ambient temperature. The solvents were evaporated and the residue purified by preparative HPLC cis and trans isomers of 1-{2-[(4-hydroxypiperidine-1-carbonyl)-amino]-ethyl}-1H-benzimidazole-5-carboxylic acid (5-hydroxyadamantan-2-yl)amide.

Provenance & Evidence