Diisopropylethylamine → HCID 86722027, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1.58 g (4.53 mmol) of 1-amino-3-bromo-N-(3,5-dichlorophenyl)-1H-pyrrole-2-carboxamide in 30 mL DMF were added 2.60 mL (14.93 mmol) of DIEA and 0.94 g (4.97 mmol) of (S)-2-(tert-butoxycarbonylamino)propanoic acid. The solution was cooled to 0° C. and 4 mL of T3P® (50% solution in DMF, 6.78 mmol) were added dropwise. The mixture was stirred at room temperature overnight and an additional 2.60 mL (14.93 mmol) of DIEA, 0.94 g (4.97 mmol) of (S)-2-(tert-butoxycarbonylamino)propanoic acid and 4 mL of T3P® (50% solution in DMF, 6.78 mmol) were added. The stirring was kept for 24 hours more and water was added to the reaction mixture. The product was extracted three times with ethyl acetate and the combined organic extracts were washed with water and brine, dried over magnesium sulphate, filtered and the solvents evaporated in vacuum. The product was purified by flash chromatography (0% to 50% hexane/AcOEt) to give 1.11 g (47% yield) of the title compound as a beige solid.

Provenance & Evidence