4,5-Dihydro-2-thiazolamine → HCID 9995482, compound

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Reaction Steps

A solution of 2-bromo-1-(3-methoxy-4-pyridin-2-ylphenyl)ethanone (200 mg, 0.65 mmol) and 2-amino-2-thiazoline (67 mg, 0.65 mmol) in ethanol (5 mL) was heated to reflux for 2 h, then concentrated. The residue was dissolved in ethyl acetate (25 mL) and washed with a solution of saturated aqueous sodium bicarbonate (10 mL) and brine (10 mL), then 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)-2,3-dihydroimidazo[2,1-b][1,3]thiazole. 1H NMR (CD3OD, 300 MHz) δ 8.86 (d, 1H), 8.67 (t, 1H), 8.35 (d, 1H), 8.17 (s, 1H), 8.04 (m, 1H), 7.84 (m, 1H), 7.62 (s, 1H), 7.54 (m, 1H), 4.60 (m, 2H), 4.26 (m, 2H), 4.07 (s, 3H) ppm. MS (ESI) 310 (M)+.

Provenance & Evidence