1,3,4-Thiadiazol-2-amine → HCID 21956514, compound

Participants

Reaction Steps

A solution of 2-bromo-1-(3-methoxy-4-pyridin-2-ylphenyl)ethanone (150 mg, 0.49 mmol) and 2-amino-1,3,4-thiadiazole (49 mg, 0.49 mmol) in ethanol (3 mL) was heated to reflux for 2 h, then concentrated. The residue was dissolved in ethyl acetate (25 mL) and washed with saturated aqueous NaHCO3 (10 mL), brine (10 mL), dried (MgSO4), and concentrated. The residue was purified by flash column chromatography on silica gel eluting with EtOAc:hexanes (2:1) to afford 6-(3-methoxy-4-pyridin-2-ylphenyl)imidazo[2,1-b][1,3,4]thiadiazole. 1H NMR (CD3OD, 300 MHz) δ 9.28 (s, 1H), 8.91 (s, 1H), 8.84 (d, 1H), 8.68 (dt, 1H), 8.37 (d, 1H), 8.05 (ddd, 1H), 7.85 (d, 1H), 7.81 (br s, 1H), 7.72 (dd, 1H), 4.09 (s, 3H) ppm. MS (ESI) 309 (M)+.

Provenance & Evidence