Dimethyl Sulfoxide → HCID 72549726, compound

Participants

Reaction Conditions

Reaction Steps

A 25 mL round bottom flask was charged with 4-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)pyridin-2(1H)-one (116 mg, 0.369 mmol) (prepared according to the procedure described in patent application WO-2009/012275), Intermediate 4 (120 mg, 0.443 mmol), quinolin-8-ol (21.4 mg, 0.148 mmol), potassium carbonate (66.3 mg, 0.480 mmol), copper(I) iodide (28.1 mg, 0.148 mmol) and DMSO (3 mL). The mixture was heated under Ar to 140° C. for 5 hours and then allowed to cool to room temperature overnight. The resulting mixture was diluted with EtOAc (100 mL) and washed with H2O (100 mL). The organic layer was concentrated in vacuo to a brown oil, which was purified by flash chromatography (SiO2, 0 to 70% Acetone in CH2Cl2) to give example 5 (73.2 mg, 39% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ 8.22 (s, 2H), 7.82 (dd, J=8.1, 5.5 Hz, 2H), 7.64 (d, J=8.4 Hz, 1H), 6.09 (dd, J=7.8, 2.6 Hz, 1H), 6.02 (d, J=2.5 Hz, 1H), 5.75 (d, J=5.7 Hz, 1H), 4.69-4.84 (m, 1H), 4.28-4.38 (m, 1H), 4.11-4.26 (m, 2H), 3.57-3.74 (m, 2H), 3.40-3.54 (m, 2H), 2.40-2.47 (m, 1H), 2.31-2.40 (m, 5H), 1.91-2.07 (m, 3H), 1.45-1.65 (m, 4H), 0.87 (t, J=7.3 Hz, 3H). MS (ESI) 505 (M+H).

Provenance & Evidence