Pyridine → Ethyl 3-(3-{5-[4-(2-bromo-5-fluorophenoxy)piperidin-1-yl]-1,3,4-thiadiazol-2-yl}-1,2,4-oxadiazol-5-yl)propanoate

Participants

Reaction Conditions

Reaction Steps

5-[4-(2-Bromo-5-fluorophenoxy)piperidin-1-yl]-N′-hydroxy-1,3,4-thiadiazole-2-carboximidamide (500 mg, 1.2 mmol) was dissolved in CH2Cl2 (5 mL) and cooled to 0° C. in an ice-water bath. To this solution was added pyridine (0.155 mL, 1.92 mmol) followed by ethyl 3-chloro-3-oxopropanoate (270 mg, 1.8 mmol). After stirring for 1 h, the solvent was removed in vacuo. The residue was dissolved in pyridine (8 mL) and stirred at 90° C. overnight. The solvent was removed and the residue was partitioned between EtOAc and water. The combined organic layers were dried over anhydrous Na2SO4, filtered and evaporated in vacuo. The crude product was purified by preparative TLC to afford the title compound.

Provenance & Evidence