1,4-Dioxane → 1-(5-(7-Chloro-2-methyl-1,6-naphthyridin-3-yl)-2-fluoro-4-methylphenyl)-3-(2-cyclobutylethyl)urea

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Reaction Steps

Treat a suspension of 3-cyclobutylpropanoic acid (0.204 g, 1.591 mmol) in dioxane (5 mL) with DPPA (0.438 g, 1.591 mmol), 5-(7-chloro-2-methyl-1,6-naphthyridin-3-yl)-2-fluoro-4-methylaniline (0.400 g, 1.326 mmol) and TEA (0.268 g, 2.65 mmol), stir at RT for 0.5 h then heat at 90° C. for 4 h. Concentrate the mixture to dryness and purify via silica gel chromatography (EtOAc/Hex) to afford the title compound (348 mg, 61%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 9.23 (d, J=0.7 Hz, 1H), 8.30 (m, 2H), 7.98 (m, 2H), 7.22 (d, J=12.3 Hz, 1H), 6.52 (t, J=5.6 Hz, 1H), 2.95 (q, J=6.5 Hz, 2H), 2.42 (s, 3H), 2.25 (m, 1H), 1.96 (m, 2H), 1.94 (s, 3H), 1.75 (m, 2H), 1.52 (m, 4H); MS(ESI) m/z: 427.1 (M+H+).

Provenance & Evidence