6-Bromo-2-(2-chloro-phenyl)-cyclohexanone → [4-(2-Chloro-phenyl)-4,5,6,7-tetrahydro-benzothiazol-2-yl]-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine

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A suspension of [3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-thiourea (69 mg, 0.26 mmol) and of crude 6-bromo-2-(2-chloro-phenyl)-cyclohexanone (79 mg, 0.28 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 (55 mg, 46%) as an off-white solid. 1H NMR (CDCl3, 300 MHz): δ (ppm)=7.77 (s, 1H), 7.46 (s, 1H), 7.35 (m, 1H), 7.13 (m, 2H), 7.08 (d, 1H), 6.96 (m, 1H), 6.85 (s, 1H), 6.68 (d, 1H), 4.53 (m, 1H), 3.54 (s, 3H), 2.77 (m, 2H), 2.33 (s, 3H), 2.24 (m, 1H), 1.80-1.99 (m, 3H).

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