Trifluoroacetic acid → HCID 73330929, compound

Participants

Reaction Steps

A solution of 3-(2-(4-(6-fluorobenzo[d]isoxazol-3-yl)piperidin-1-yl)ethyl)-2-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl 3-pivalamidopropanoate, prepared as described in Step A, (901.5 mg, 1.15 mmol) in dichloromethane (20 mL) and trifluoroacetic acid (5.7 mL) was stirred for 1 h at room temperature. To this mixture was carefully added a solution of N-maleoyl-3-aminopropionic acid (233.8 mg, 1.38 mmol), diisopropylethylamine (13.94 mL), diethyl cyanophosphonate (306.57 μL, 1.81 mmol) and dichloromethane (2 mL). The reaction mixture was stirred for 1 h at room temperature under argon atmosphere. The reaction mixture was poured into water (20 mL) and the aqueous layer extracted with dichloromethane (three times 20 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated. The crude mixture was purified on HPLC to give the title compound. ESI-MS (M+1) 649.

Provenance & Evidence