2-Oxopropanethioamide → 5'-Bromo-4-methoxy-5''-methyldispiro[cyclohexane-1,2'-[1]-benzofuran-3',2''-imidazole]-4''(3''H)-thione

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5-Bromo-4′-methoxy-3H-spiro[benzofuran-2,1′-cyclohexan]-3-imine (Example 29 Step 2, 1.37 g, 4.41 mmol) and 2-oxopropanethioamide (Intermediate 2, 0.909 g, 8.81 mmol) were dissolved in dry MeOH (25 mL) and the resulting orange solution was heated at 60° C. under a nitrogen atmosphere overnight. More 2-oxopropanethioamide (400 mg) was added and stirring continued. After 24 h the mixture was allowed to cool to r.t. and the solvent was evaporated. Purification by flash chromatography using a gradient of 0-100% EtOAc in heptane afforded 373 mg of the title compound (21% yield). 1H NMR (500 MHz, DMSO-d6) δ ppm 1.35 (m, 1H), 1.47 (m, 3H), 1.87 (m, 2H), 1.97 (m, 2H), 2.29 (s, 3H), 3.13 (s, 3H), 4.11 (m, 1H), 6.99 (d, 1H), 7.16 (d, 1H), 7.48 (dd, 1H); MS (ES+) m/z 396 [M+H]+.

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