Methyl 1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxylate → HCID 117844227, compound

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Reaction Steps

A mixture of 4-cyano-1,1-dioxo-hexahydro-1λ6-thiopyran-4-carboxylic acid tert-butyl ester (208 mg) and Raney Ni (0.5 mL in water) in MeOH (20 mL) was stirred at rt under H2 atmosphere (balloon) overnight. Then the reaction mixture was filtered over Celite pad, filtrate was concentrated to give the desired product 4-aminomethyl-1,1-dioxo-hexahydro-1λ6-thiopyran-4-carboxylic acid tert-butyl ester (212 mg), which was used in the next step. A mixture of 1-cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (24 mg) and 4-aminomethyl-1,1-dioxo-hexahydro-1λ6-thiopyran-4-carboxylic acid tert-butyl ester (45 mg) in EtOH (1 mL) was microwaved at 140° C. for 2 h. The mixture was cooled, concentrated and the residue was column purified to give the desired product (5 mg). LC MS ESI+: 552 (M+1)+.

Provenance & Evidence