Hydrochloric Acid → HCID 58877841, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3′-(benzyloxy)-4′-oxo-2,3,4′,5,6,6′,7′,9′-octahydrospiro[pyran-4,10′-pyrimido[1,2-d][1,4]oxazepine]-2′-carboxylic acid (0.095 g, 0.246 mmol) in CH3CN (15 mL) was added 1-(2-(aminomethyl)-5-fluorophenyl)-4-methyl-1H-1,2,4-triazol-5(4H)-one (0.070 g, 0.271 mmol), diisopropylethylamine (0.171 mL, 0.984 mmol) and O-(7-azabenzotriazole-1yl)-N,N,N′,N′-tetramethyluronium (0.103 g, 0.271 mmol). The reaction mixture was stirred at 23° C. for 18 hours. HCl (1N, 50 mL) was added and the organic material was extracted with EtOAc (3×50 mL). The combined organic phases were washed with H2O (50 mL), brine (50 mL), dried over MgSO4 and concentrated in vacuo. The crude material was purified on Silica gel column (Biotage™), eluted with EtOAc:Hex (1:1) to EtOAc 100% to afford the title compound as a white solid (0.130 g, 77%): 1H NMR (400 MHz, CDCl3) δ 8.54 (1 H, brs), 7.67 (1H, dd, J=8.7, 6.2 Hz), 7.52 (2H, m), 7.45 (1H, s), 7.27-7.36 (3H, m), 7.22 (1H, dd, J=9.3, 2.5 Hz), 7.08 (1H, td, J=8.2, 2.5 Hz), 5.31 (2H, s), 4.54 (2 H, d, J=6.3 Hz), 4.1-3.6 (10H, m), 3.36 (3H, s), 2.4-2.2 (1H, brm), 2.1-1.6 (2H, brs). LCMS (+ESI, M+H+) m/z 591.

Provenance & Evidence