4-Methylmorpholine → N-[1-(4-Cyano-3-fluoro-phenyl)-1-(3-methyl-3H-imidazol-4-yl)-ethyl]-3-(3-methoxy-benzenesulfonylamino)-propionamide

Participants

Reaction Steps

To a solution of 3-(3-methoxy-benzenesulfonylamino)-propionic acid (0.261 g, 1.01 mmol) in DMF (4 mL) at room temperature was added 1-hydroxybenzotriazole hydrate (HOBT) (0.146 g, 0.96 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC) (0.202 g, 1.05 mmol), 4-methylmorpholine (0.102 g, 1.01 mmol), and (+)-4-[1-amino-1-(3-methyl-3H-imidazol-4-yl)-ethyl]-2-fluoro-benzonitrile (Step I) (0.246 g, 1.01 mmol). After stirring overnight, the reaction was concentrated in vacuo. The residue was partitioned between EtOAc and water, the organic layer separated, washed with brine, dried (Na2SO4), and concentrated in vacuo to provide the title compound after purification by chromatography on silica gel (5% to 7.5% methanol/0.1% ammonium hydroxide in CH2Cl2).

Provenance & Evidence