Diisopropylethylamine → HCID 67095667, compound

Participants

Reaction Steps

To a mixture rac-4-{[(2S,3S,4S)-2-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-3-cyano-4-(2,2-dimethyl-propyl)-pyrrolidine-1-carbonyl]-amino}-butyric acid (24.0 mg, 0.043 mmol, Example 58) in N,N-dimethyl formamide (2.5 mL) was added DIPEA (48.2 mg, 0.373 mmol), HoBt (12.2 mg, 0.090 mmol), HBTU (30.7 mg, 0.081 mmol) and methylamine hydrochloride (9.6 mg, 0.142 mmol). After it was stirred at rt for 5.5 hrs, the solvent was removed and the reaction mixture was extracted with EtOAc, and washed with 1N sodium hydroxide (2×), water, and saturated NaCl. The organic phase was separated, and dried over Na2SO4. The reaction mixture was then purified by flash column to give rac-(2S,3S,4S)-2-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-3-cyano-4-(2,2-dimethyl-propyl)-pyrrolidine-1-carboxylic acid (3-methylcarbamoyl-propyl)-amide (23.0 mg, 93.7%). HRMS (ES+) m/z Calcd for C28H32Cl2F2N4O2+H [(M+H)+]: 565.1943; Found: 565.1944.

Provenance & Evidence