Hydrochloric Acid → (racemic) N-(5-cyano-4-(quinuclidin-3-yloxy)pyridin-2-yl)-7-formyl-6-(hydroxymethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide

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Reaction Steps

Aqueous hydrochloric acid (3 M, 1 ml) was added to a solution of racemic 6-(((tert-butyldimethylsilyl)oxy)methyl)-N-(5-cyano-4-(quinuclidin-3-yloxy)pyridin-2-yl)-7-(dimethoxymethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide (intermediate 78, 120 mg, 0.193 mmol) in THF (1.6 ml) at room temperature. After stirring for 100 min saturated aqueous NaHCO3 was added, the mixture extracted with DCM (3×), the organic layers dried over Na2SO4 and evaporated. The residue was sonicated with EtOAc (2 ml) and hexanes (2 ml) and then filtered to give the title compound as an off-white solid.

Provenance & Evidence