Morpholine → N-(4-((6-(3-pivaloylureido)pyridin-3-yl)oxy)pyridin-2-yl)morpholine-4-carboxamide

Participants

Reaction Steps

A mixture of Example C2 (0.145 g, 0.351 mmol), morpholine (0.092 g, 1.052 mmol) and N-methylpyrrolidine (2.99 mg, 0.035 mmol) in dioxane (3 mL) was heated at 80° C. overnight, cooled to RT, concentrated to dryness and purified via silica gel chromatography (MeOH/DCM) to afford N-(4-((6-(3-pivaloylureido)pyridin-3-yl)oxy)pyridin-2-yl)morpholine-4-carboxamide (80 mg, 52%). 1H NMR (400 MHz, DMSO-d6): δ 11.22 (s, 1H), 10.43 (s, 1H), 9.29 (s, 1H), 8.23 (d, J=2.9 Hz, 1H), 8.13 (d, J=5.7 Hz, 1H), 8.08 (d, J=9.0 Hz, 1H), 7.71 (dd, J=9.0, 2.9 Hz, 1H), 7.37 (d, J=2.4 Hz, 1H), 6.62 (dd, J=5.7, 2.4 Hz, 1H), 3.53 (m, 4H), 3.39 (m, 4H), 1.21 (s, 9H); MS (ESI) m/z: 443.2 (M+H+).

Provenance & Evidence