Water → HCID 24965849, compound

Participants

Reaction Steps

A solution of 2-(3-(piperidin-4-ylidenemethyl)phenoxy)-5-(trifluoromethyl)pyridine hydrochloride (0.100 g; Example 1a, Step 5), phenyl 5-acetyl-4-methylthiazol-2-ylcarbamate (0.089 g, 1.2 equiv), and triethylamine (0.045 mL, 1.2 equiv) in dimethyl sulfoxide (1 mL, 0.3 M) was heated to 65° C. for 2 h. The reaction was cooled to room temperature. Water was added and then the solution was extracted with ethyl acetate (2×). The organic extracts were dried over magnesium sulfate, filtered, and concentrated. The residue was purified on a 12 g silica gel column using 10-30% ethyl acetate/dichloromethane over 20 minutes as the eluent to give the title compound as a light yellow foam. 0.065 g, 47% yield. 1H NMR (400 MHz, CDCl3) δ ppm 2.44-2.54 (5H, m), 2.61 (2H, t, J=5.7 Hz), 2.66 (3H, s), 3.63 (2H, t, J=5.8 Hz), 3.73 (2H, t, J=5.9 Hz), 6.42 (1H, s), 6.92-7.04 (3H, m), 7.07 (1H, d, J=7.8 Hz), 7.38 (1H, t, J=8.0 Hz), 7.89 (1H, dd, J=8.6, 2.7 Hz), 8.43 (1H, s).

Provenance & Evidence