Triethylamine → HCID 178426913, compound

Participants

Reaction Steps

To a solution of 10-amino-2-(4-(4-fluorobenzyl)-1H-imidazol-2-yl)-3-hydroxy-7,8,9,10-tetrahydro-7,10-ethanopyrimido[1,2-a]azepin-4(6H)-one, Example 1 (30 mg, 0.076 mmol) in CH2Cl2 (3 mL) was added triethylamine (0.063 mL, 0.455 mmol) followed by 5-methylisoxazole-3-carbonyl chloride (55.2 mg, 0.379 mmol) and the resulting mixture stirred at room temperature. After 16 h the reaction mixture was concentrated to give the crude product which was treated with 2M dimethylamine/MeOH (0.5 mL) in MeOH (2 mL) at 60° C. for 2 h. The mixture was then cooled and purified by preparative HPLC to afford the title compound (15 mg, 39%) as a white solid. 1H NMR (500 MHz, DMSO-d6) δ ppm 13.4 (1H, br. s.), 9.0 (1H, s), 7.4 (1H, br. s.), 7.4 (2H, dd, J=8.24, 5.80 Hz), 7.2 (2H, t, J=8.85 Hz), 6.6 (1H, s), 4.1 (2H, d, J=3.36 Hz), 4.1 (2H, s), 2.7-2.8 (2H, m), 2.5 (1H, br. s.), 2.0-2.0 (2H, m), 1.9-1.9 (2H, m), 1.7-1.8 (2H, m). LCMS (M+H)=505.49.

Provenance & Evidence