Diisopropylethylamine → N'-(2-((3-(4-Fluorophenyl)-2-oxopropyl)carbamoyl)-3-hydroxy-4-oxo-6,7,8,9-tetrahydro-7,10-ethanopyrimido[1,2-a]azepin-10(4H)-yl)-N,N-dimethylethanediamide

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To a solution of 10-amino-N-(3-(4-fluorophenyl)-2-oxopropyl)-3-hydroxy-4-oxo-4,6,7,8,9,10-hexahydro-7,10-ethanopyrimido[1,2-a]azepine-2-carboxamide, Intermediate 14 (318 mg, 0.705 mmol) in DMF (8 mL) were added 2-(dimethylamino)-2-oxoacetic acid (165 mg, 1.411 mmol), N,N-diisopropylethylamine (0.739 mL, 4.23 mmol), HATU (536 mg, 1.411 mmol) and DMAP (17.23 mg, 0.141 mmol) and the resulting mixture was stirred at room temperature for 3 h. The mixture was then purified by preparative HPLC to afford the title compound (210 mg, 0.409 mmol, 58.0% yield) as an off-white solid. 1H NMR (500 MHz, CDCl3) δ ppm 11.67 (1H, br. s.), 8.54 (1H, t, J=5.49 Hz), 8.03 (1H, s), 7.19 (2H, dd, J=8.55, 5.19 Hz), 6.99-7.05 (2H, m), 4.26 (2H, d, J=5.49 Hz), 4.17 (2H, d, J=3.97 Hz), 3.77 (2H, s), 3.28 (3H, s), 2.92 (3H, s), 2.46-2.57 (5H, m), 2.09-2.17 (2H, m), 1.91-2.01 (2H, m), 1.67-1.77 (2H, m). LCMS (M+H)=514.26.

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