Hydrochloric Acid → 4-(1-(4-hydroxy-4-phenylcyclohexyl)-4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-3-yl)thiophene-2-carboxamide

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Reaction Steps

To a solution of 4-(4-oxo-1-(4-oxocyclohexyl)-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-3-yl)thiophene-2-carboxamide (30.0 mg) obtained in Example 170 in THF (10 mL) was added dropwise 1.6 M phenyllithium butyl ether solution (0.210 mL) at −78° C., and the mixture was stirred overnight at room temperature. To the reaction mixture was added dropwise 1N hydrochloric acid at 0° C., and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/methanol) to give the title compound (cis/trans mixture, 11.2 mg).

Provenance & Evidence