Hydrochloric Acid → HCID 89462837, compound

Participants

Reaction Conditions

Reaction Steps

A 6 mL microwave vial was charged with 2-(5-(4-fluorobenzyl)-7-methyl-6-oxo-9-(p-tolyl)-1,3,4,5,6,7-hexahydropyrano[3′,4′:4,5]pyrrolo[2,3-c]pyridin-8-yl)-2-((tetrahydro-2H-pyran-2-yl)oxy)acetonitrile (170 mg, 0.314 mmol), Ethanol (5 ml) and 20% NaOH (2.54 ml, 14.60 mmol). The reaction vessel was sealed and heated in a 140° C. oil bath. After 18 h, the reaction mixture was cooled in an ice bath and conc HCl was added until pH <2. The residue was suspended in a mixture of MeOH (2 mL) and Et2O (2 mL), cooled to 0° C. and treated dropwise with TMS diazomethane (0.628 ml, 1.256 mmol). The reaction mixture was concentrated in vacuo and purified by ISCO (0-50% EtOAc-hexanes) to afford methyl 2-(5-(4-fluorobenzyl)-7-methyl-6-oxo-9-(p-tolyl)-1,3,4,5,6,7-hexahydropyrano[3′,4′:4,5]pyrrolo[2,3-c]pyridin-8-yl)-2-hydroxyacetate (26 mg, 0.053 mmol, 16.89% yield) as a white solid. LCMS (m/z) ES+=491 (M+1).

Provenance & Evidence