Methyl 1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxylate → HCID 117843666, compound

Participants

Reaction Steps

A mixture of 4-cyano-1-oxo-hexahydro-1λ4-thiopyran-4-carboxylic acid tert-butyl ester (193 mg) and Raney Ni (0.5 mL in water) in MeOH (30 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-oxo-hexahydro-1λ4-thiopyran-4-carboxylic acid tert-butyl ester (195 mg), which was used in the next step. A mixture of 1-cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (35 mg) and 4-aminomethyl-1-oxo-hexahydro-1λ4-thiopyran-4-carboxylic acid tert-butyl ester (52 mg) in EtOH (1.5 mL) was refluxed overnight. The mixture was cooled, concentrated and the residue was column purified to give the desired product (23 mg). LC MS ESI+: 536 (M+1)+.

Provenance & Evidence