1,2-Dichloroethane → HCID 59271827, compound

Participants

Reaction Steps

To a mixture of N-(4-fluoro-3-methylbenzyl)-3-hydroxy-7,7-dimethyl-10-(methylamino)-4-oxo-4,6,7,8,9,10-hexahydropyrimido[1,2-a]azepine-2-carboxamide hydrochloride (200 mg, 0.421 mmol), HOAt (68.7 mg, 0.5 mmol), N,N-dimethyloxamic acid (74 mg, 0.631 mmol) and triethylamine (0.235 mL, 1.683 mmol), in dichloromethane (5 mL) was added EDC (224 mg, 1.262 mmol). The mixture was stirred at room temperature under nitrogen overnight, diluted with 25 mL EtOAc, washed with 10 mL each of saturated NaHCO3 solution, H2O, and brine, and dried over Na2SO4. Concentration gave a crude title product which was purifried by preparative reverse phase chromatography (gradient elution 0.1% AcOH in water/acetonitrile) to give the title product as a solid: HRMS (ES+): 502.2484 (M+H); 1H NMR (400 MHz, CDCl3) δ 9.35 (br s, 3H), 7.2 (m, 2H), 6.9 (t, J=9 Hz, 1H), 5.34 (br s, 1H), 4.8 (d, J=14 Hz, 1H), 4.5 (m, 21H), 4.5 (m, 2H), 3.3 (d, J=14 Hz, 1H), 3.0 (s, 3H), 2.98, (s, 3H), 2.96 (s, 3H), 2.2 (s, 3H), 2.0 (m, 2H), 1.9 (m, 1H), 1.7 (s, 2H), 1.12 (s, 3H), 0.83 (s, 3H).

Provenance & Evidence