Water → HCID 86645656, compound

Participants

Reaction Steps

At 0° C., into a solution of methyl 2-fluoro-4-{5-[2-(hydroxymethyl)-2′-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzoate, prepared as in example 58, step 1, (500 mg; 1.19 mmol) in DCM (15 mL) was added DIEA (610 μL; 3.58 mmol) and methanesulfonyl chloride (139 μL; 1.79 mmol). The reaction was allowed to warm to RT for 2 h30. Water (5 mL) was added and the DCM extract was rapidly washed twice more with water. The organic layer was then dried over magnesium sulfate, filtered and concentrated to afford the title compound as a yellow foam (573 mg; 97%). 1H NMR (DMSO-d6, 300 MHz) δ 8.47 (d, J=1.8 Hz, 1H), 8.30 (dd, J=8.0, 1.8 Hz, 1H), 8.18-8.13 (m, 1H), 8.09 (dd, J=8.1, 1.5 Hz, 1H), 8.02 (dd, J=11.2, 1.4 Hz, 1H), 7.54 (d, J=8.0 Hz, 1H), 7.40-7.29 (m, 3H), 7.19 (d, J=7.0 Hz, 1H), 5.11 (d, J=11.4 Hz, 1H), 5.05 (d, J=11.4 Hz, 1H), 3.92 (s, 3H), 3.04 (s, 3H), 2.05 (s, 3H). LC/MS (Method B): 497.3 (M+H)+. HPLC (Method A) Rt 5.52 min (Purity: 96.7%).

Provenance & Evidence