Pyridine → HCID 57586409, compound

Participants

Reaction Steps

To a solution of 3-(5-(4-aminophenyl)-1,2,4-thiadiazol-3-yl)-1-(3,3-diphenylpropyl)-1-(2-(pyridin-2-yl)ethyl)urea (0.042 g, 0.079 mmol), prepared in the previous step, in DCM (1.5 mL) at 0° C. was added pyridine (50 μL, 49 mg, 0.62 mmol) and acetic anhydride (9.0 μL, 9.0 mg, 0.088 mmol). The reaction mixture was warmed to room temperature. After 1 h, additional acetic anhydride (10 μL) and a small amount of DMAP were added. Stirring was continued at room temperature. After 3 h, the reaction mixture was diluted with EtOAc, washed with saturated NaHCO3 (1×), brine (1×), dried over MgSO4, filtered, and concentrated. The crude reaction mixture was dissolved in DCM (˜2 mL) and diluted with ˜5 mL of hexanes. The precipitate was collected by filtration and dried under high vacuum to give N-(4-(3-(((3,3-diphenylpropyl)(2-(2-pyridinyl)ethyl)carbamoyl)amino)-1,2,4-thiadiazol-5-yl)phenyl)acetamide 158. Mass spectrum, calculated for C33H32N6O2S 576.2; found 577.2 (M++1).

Provenance & Evidence