Water → HCID 178490689, compound

Participants

Reaction Steps

To a solution of Example 18A (2.65 g, 9.4 mmol) in N,N-dimethylformamide (20 mL) at 0° C. was added sodium hydride (60% dispersion in mineral oil, 0.247 g, 10.3 mmol). The reaction mixture was stirred for 30 min. and then treated with commercially available 4-(chloromethyl)thiazole (1.25 g, 9.4 mmol). The resulting mixture was stirred at room temperature for 18 h, poured into water (100 mL) and extracted with ethyl acetate (2×100 mL). The organics were washed with water, brine (2×100 mL), dried over MgSO4, filtered, and concentrated. The residue was purified by using an Analogix® Intelliflash280™ (SiO2, 0-50% ethyl acetate in hexanes) to afford the title compound (2.56 g, 72% yield). 1H NMR (300 MHz, DMSO-d6) δ ppm 2.28 (s, 3H), 3.77 (s, 3H), 5.50 (s, 2H), 7.10 (d, J=8.7 Hz, 1H), 7.31 (d, J=1.6 Hz, 1H), 7.38-7.52 (m, 2H), 7.63 (dd, J=14.5, 2.6 Hz, 1H), 9.09 (d, J=2.0 Hz, 1H). MS (DCI) m/z 398 (M+H)+; MS (DCI) m/z 380 (M+H)+. Anal. Calculated for C16H14ClN3O2S2: C, 50.59; H, 3.71; N, 11.06. Found: C, 50.57; H, 3.02; N, 11.03.

Provenance & Evidence