Morpholine → N-(4-(2,6-dichlorobenzamido)pyridin-2-yl)-2-morpholinothiazole-5-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a suspension of 2-bromo-N-(4-(2,6-dichlorobenzamido)pyridin-2-yl)thiazole-5-carboxamide (Example 7) (24.0 mg, 0.051 mmol) in 1-butanol (1 mL) was added morpholine (44.4 mg, 0.51 mmol). The mixture was heated at 50° C. for 6 hours. The mixture was then concentrated under reduced pressure, and the residue was purified by reverse-phase HPLC (Gemini, 3×10 cm, gradient: 5-85% CH3CN/H2O with 0.1% NH4OH over 10 min) to afford the desired product (17 mg, 69.4% yield). 1H NMR (400 MHz, DMSO) δ 11.18 (s, 1H), 10.68 (s, 1H), 8.38 (s, 1H), 8.32 (s, 1H), 8.27 (d, J=5.5, 1H), 7.63-7.57 (m, 2H), 7.56-7.51 (m, 2H), 3.73-3.68 (m, 4H), 3.52-3.46 (m, 4H). LCMS (ESI) m/z: 478.2 [M+H+]

Provenance & Evidence