Ethanol → 4,5,6,7-Tetrahydro-N-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-4-(2-methoxyphenyl)-2-benzothiazolamine

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A suspension of [3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-thiourea (43 mg, 0.16 mmol) and of crude 2-bromo-6-phenyl-cyclohexanone (49 mg, 0.17 mmol) in ethanol (2 mL) was heated to reflux under an atmosphere of nitrogen for 2 days. After cooling to room temperature the solvent was evaporated under reduced pressure and the residue was purified by reversed preparative HPLC using acetonitril/water (0.1% formic acid) to yield the title compound (15 mg, 21%) as a yellow gum. MS ISP (m/e): 447.3 (100) [(M+H)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=7.59 (s, 1H), 7.29 (s, 1H), 7.07-7.18 (m, 2H), 6.82-6.88 (m, 4H), 6.65 (d, 1H), 4.49 (m, 1H), 3.84 (s, 3H), 3.57 (s, 3H), 2.89 (m, 2H), 2.88 (s, 3H), 2.14 (m, 1H), 1.70-1.91 (m, 3H).

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