Triethylamine → HCID 58458928, compound

Participants

Reaction Steps

A mixture of 3-(benzyloxy)-9,9-dimethyl-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carboxylic acid (prepared according to the procedure in Naidu, B. N. et al WO2005118593) (0.495 g, 1.5 mmol), 1-amino-3-(4-fluorophenyl)propan-2-one hydrochloride (prepared according to the procedure in Maeda, S. et al Chem. Pharm. Bull. 1984, 32, 2536-2543; 0.406 g, 2 mmol), HATU (0.760 g, 2 mmol), Et3N (0.56 mL, 4 mmol) and DMAP (60 mg) in DMF (15 mL) was stirred at room temperature. After 4 h, the reaction mixture was diluted with Et2O (100 mL), washed with water (3×10 mL), brine (10 mL), dried (Na2SO4), filtered and concentrated to give the title compound (0.57 g, 78% yield) as a viscous yellow oil which was used in the subsequent step without purification. 1HNMR (500 MHz, CDCl3) δ: 8.10-8.07 (1H, br s), 7.56 (2H, d, J=7.3 Hz), 7.34-7.28 (3H, m), 7.19 (2H, dd, J=8.6, 5.5 Hz), 7.03 (2H, t, J=8.6 Hz), 5.29 (2H, s), 4.30 (2H, d, J=4.9 Hz), 4.04-3.98 (4H, m), 3.75 (2H, s), 2.79 (6H, s), 1.62 (6H, s). HRMS (M+H) calcd for C26H27N3O5F: 480.1935. found: 480.1930.

Provenance & Evidence