1-Hydroxybenzotriazole → HCID 117643868, compound

Participants

Reaction Steps

To a 50 mL round-bottom flask were added (S)-4-(5-bromo-2-chloropyrimidin-4-yl)morpholine-3-carboxylic acid (560 mg, 1.736 mmol), 1-hydroxybenzotriazole (235 mg, 1.736 mmol), and 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (399 mg, 2.083 mmol) in THF (10 mL) at 0° C. to give a beige solution. After 5 minutes, (S)-1-(4-chlorophenyl)ethylamine (0.268 mL, 1.910 mmol) was added to the solution, which was allowed to react at 0° C. for 2 hours. The reaction mixture was subsequently partitioned between brine and ethyl acetate. The aqueous layer was extracted with ethyl acetate and the combined organic layers were dried over MgSO4, filtered, and concentrated. The residue was purified by normal phase column chromatography (20-50% EtOAc gradient in hexanes for 20 minutes) to give the title compound as a white foam (701 mg, 88%). ESI-MS m/z [M+H]+ calc'd for C17H17BrCl2N4O2, 458.99; found 459.3.

Provenance & Evidence