Hydrochloric Acid → HCID 118036533, compound

Participants

Reaction Steps

Racemic 6-(((tert-butyldimethylsilyl)oxy)methyl)-N-(5-cyano-4-(((1S*,2R*,3S*,4R*)-3-(((triethylsilyl)oxy)methyl)bicyclo[2.2.1]heptan-2-yl)amino)pyridin-2-yl)-7-(dimethoxymethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide (intermediate 37N, 64 mg, 0.085 mmol) was dissolved in THF (2 ml) and water (1 ml) and treated with conc. HCl (0.28 ml). The reaction mixture was stirred 30 h at room temperature. The reaction mixture was then quenched with sat. aq. NaHCO3 and extracted 3× with DCM. The organic layer was dried over Na2SO4, filtered and concentrated under vacuum. The residue was triturated in a small quantity of DCM and then, the product was precipitated by addition of heptanes. The solid was collected by centrifugation and dried to give the title compound as a white solid.

Provenance & Evidence