Diisopropylethylamine → HCID 58431092, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (S)-2-{[(R)-5-(4-cyano-benzyl)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carbonyl]-amino}-propionic acid, (129 mg, 0.25 mmol), (R)-2-amino-thiopropionamide hydrochloride (53 mg, 0.38 mmol) and diisopropylethylamine (0.175 mL, 1.01 mmol) in DMF (1 mL) was stirred at room temperature for 10 min. After cooling to 0° C., HOAt (69 mg, 0.50 mmol) and HATU (105 mg, 0.25 mmol) were added. The clear yellow reaction mixture was allowed to warm to room temperature slowly overnight. The reaction mixture was partitioned between ethyl acetate (35 mL) and 1 M HCl (10 mL). The organic phase was washed with saturated NaHCO3 solution and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (0-10% MeOH in dichloromethane) to afford 154 mg of the title compound as a white foam, m/z 598.4 [M+1]+.

Provenance & Evidence