Methyl vinyl sulfone → HCID 57670165, compound

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Reaction Steps

To a stirred solution of [(4S,5R)-2-(6-tert-butyl-4-ethoxy-pyridin-3-yl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazol-1-yl]-(4-hydroxy-piperidin-1-yl)-methanone (94.8 mg, 0.152 mmole, example 101) was added sodium hydride (9.3 mg, 0.232 mmole, 60%, Aldrich) followed by methyl vinyl sulfone (0.04 mL, 0.448 mmole, Aldrich). The mixture was allowed to stir at room temp for 2.5 h before quenched with aqueous ammonium chloride and extracted with dichloromethane. The organic extracts were washed with brine and concentrated to dryness. The crude product was purified by flash column chromatography (silica gel, eluting a gradient of 1-10% methanol in methylene chloride) to give the title compound (93.4 mg, 84% yield). HR-MS (ES, m/z) calculated for C37H47Cl2N4O5S [(M+H)+] 729.2639, observed 729.2641.

Provenance & Evidence