Ethyl Acetate → 1-(3,3-Dimethylbutyl)-3-(2-fluoro-5-(7-((4-methoxybenzyl)(methyl)amino)-2-methyl-1,6-naphthyridin-3-yl)phenyl)urea

Participants

Reaction Conditions

Reaction Steps

Treat a solution of prop-1-en-2-yl(2-fluoro-5-(7-((4-methoxybenzyl)(methyl)amino)-2-methyl-1,6-naphthyridin-3-yl)phenyl)carbamate (0.398 g, 0.818 mmol) and 3,3-dimethylbutylamine (0.166 g, 1.636 mmol) in dioxane (10 mL) with DBU (0.025 ml, 0.164 mmol) and heat at 80° C. overnight. Cool to RT, add EtOAc and wash with 10% LiCl, then brine. Dry the organic layer over MgSO4, concentrate to dryness and purify via silica gel chromatography (EtOAc/Hex) to afford the title compound (370 mg, 85%). 1H NMR (400 MHz, DMSO-d6): δ 8.97 (s, 1H), 8.37 (s, 1H), 8.22 (d, J=7.9 Hz, 1H), 7.99 (s, 1H), 7.26 (dd, J=11.4, 8.4 Hz, 1H), 7.15 (d, J=8.4 Hz, 2H), 6.98 (m, 1H), 6.85 (d, J=8.5 Hz, 2H), 6.73 (s, 1H), 6.55 (t, J=5.5 Hz, 1H), 4.86 (s, 2H), 3.69 (s, 3H), 3.08 (m, 5H), 2.48 (s, 3H), 1.33 (m, 2H), 0.88 (s, 9H); MS (ESI) m/z: 530.0 (M+H+).

Provenance & Evidence