N-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-5-chloro-2-methoxybenzamide → HCID 178490684, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of Example 4A (200 mg, 0.62 mmol) in N,N-dimethylformamide/tetrahydrofuran (1:4, 10 mL) were added a solution of potassium tert-butoxide (Aldrich, 103 mg, 0.92 mmol) and Example IB (189 mg, 0.74 mmol). The reaction mixture was stirred at 80° C. for 16 h, cooled to room temperature, quenched with saturated aqueous NaHCO3 (10 mL). The aqueous layer was extracted with ethyl acetate (3×10 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-1% methanol in dichloromethane) to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.39 (s, 9H), 1.69-2.04 (m, 4H), 3.60-3.70 (m, 1H), 3.73-3.79 (m, 1H), 3.80 (s, 3H), 4.24 (dd, J=4.7, 15.0 Hz, 1H), 4.31-4.42 (m, 1H), 4.49 (dd, J=15.0, 7.5 Hz, 1H), 7.14 (d, J=8.8 Hz, 1H), 7.50 (dd, J=8.8, 2.7 Hz, 1H), 7.73 (d, J=3.1 Hz, 1H); MS (ESI+) m/z 410 (M+H)+.

Provenance & Evidence