Diisopropylethylamine → 1-(7,8-Bis(4-chlorophenyl)-3-oxo-2,3-dihydro-[1,2,4]triazolo[4,3-c]pyrimidin-5-yl)-3-(ethylamino)azetidine-3-carboxamide

Participants

Reaction Steps

To a stirred suspension of 3-(ethylamino)azetidine-3-carboxamide (25 mg, 0.17 mmol) in EtOH (1.0 mL) at room temperature under argon was added N,N-diisopropylethylamine (60 mg, 0.46 mmol). The reaction mixture was stirred at room temperature for 10 min to obtain a clear solution to which was added 5-chloro-7,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one (60 mg, 0.15 mmol). The reaction mixture was stirred at 60° C. in a pre-heated oil bath for 5 min. The reaction mixture was then concentrated under reduced pressure, and the residue was dissolved in CH2Cl2 (5 mL). The resulting mixture was washed with water (2 mL×2), dried (MgSO4), and concentrated under reduced pressure to obtain the crude product. This crude product was purified by preparative reverse phase HPLC (without TFA) to obtain 35 mg of the title compound as a pale yellow solid. HPLC/MS: retention time=3.306 min, [M+H]30 =498.

Provenance & Evidence