Acetamide → HCID 86270222, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of Example C8 (0.243 g, 0.518 mmol), acetamide (0.184 g, 3.11 mmol), Cs2CO3 (0.422 g, 1.294 mmol) and Xantphos (0.090 g, 0.155 mmol) in dioxane (3 mL) was sparged with Ar, treated with Pd2(dba)3 (0.062 g, 0.067 mmol), sparged again with Ar and heated at 100° C. overnight. The mixture was cooled to RT, treated with brine, extracted with EtOAc (3×) and the combined organics were dried over Na2SO4, concentrated to dryness and purified twice via silica gel chromatography (MeOH/DCM, then MeOH/EtOAc) to afford N-(4-((2-acetamidopyridin-4-yl)oxy)-5-chloro-2-fluorophenyl)-2-oxo-3-(tetrahydro-2H-pyran-4-yl)imidazolidine-1-carboxamide (74 mg, 29%). 1H NMR (400 MHz, DMSO-d6): δ 10.92 (d, J=2.7 Hz, 1 H), 10.57 (s, 1 H), 8.39 (d, J=8.1 Hz, 1 H), 8.17 (d, J=5.7 Hz, 1 H), 7.61 (d, J=2.4 Hz, 1 H), 7.58 (d, J=11.2 Hz, 1 H), 6.64 (dd, J=5.7, 2.4 Hz, 1 H), 3.93-3.83 (m, 3 H), 3.81 (m, 2 H), 3.48 (t, J=8.2 Hz, 2 H), 3.37 (dd, J=12.4, 10.6 Hz, 2 H), 2.03 (s, 3 H), 1.71 (qd, J=12.2, 4.5 Hz, 2 H), 1.62-1.56 (m, 2H); MS (ESI) m/z: 492.1 (M+H+).

Provenance & Evidence