Dimethylamine → HCID 57904918, compound

Participants

Reaction Steps

A solution of N-(4-fluorobenzyl)-3-hydroxy-10-((2-hydroxyethyl)amino)-4-oxo-4,6,7,8,9,10-hexahydro-7,10-ethanopyrimido[1,2-a]azepine-2-carboxamide (0.3358 g, 0.633 mmol) in CH2Cl2 (10 mL) with diisopropyl ethylamine (0.553 mL, 3.17 mmol) was cooled to 0° C. Methyl 2-chloro-2-oxoacetate (0.233 mL, 2.53 mmol) was added and the yellow solution stirred for 5 h, gradually warming to room temperature. The reaction was quenched with water and the organic phase was washed with 1N HCl, dried (Na2SO4), filtered and concentrated to give a yellow foam which was dissolved in hot ethanol (10 mL) and treated with 2M dimethylamine (1.583 mL, 3.17 mmol). The resulting yellow solution was stirred in a sealed tube at 85° C. for 18 h. The solution was concentrated and purified by preparative HPLC to give the title compound as a white solid (0.1692 g, 52% yield). 1H NMR (500 MHz, CDCl3) δ: 12.20 (1 H, brs), 9.71 (1 H, brs), 7.34 (2 H, dd, J=8.55, 5.49 Hz), 6.98 (2 H, t, J=8.70 Hz), 4.69 (1 H, dd, J=15.56, 7.63 Hz), 4.50-4.57 (1 H, m), 4.37-4.48 (2 H, m), 3.84-3.91 (1 H, m), 3.75-3.81 (1 H, m), 3.56-3.70 (3 H, m), 3.41-3.51 (1 H, m), 2.97 (3 H, s), 2.96 (3 H, s), 2.49 (1 H, brs), 1.98-2.14 (3 H, m), 1.71-1.91 (3 H, m), 1.38-1.47 (1 H, m). LCMS (M+H)=516.07. HPLC purity: >95%.

Provenance & Evidence