Pyridine → HCID 68470577, compound

Participants

Reaction Steps

0.5 g of methyl 7-amino-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate is dissolved under an inert atmosphere in 5 cm3 of dichloromethane at a temperature close to 20° C. 0.142 cm3 of pyridine is poured into the reaction mixture which is then cooled to a temperature close to 5° C. 0.122 cm3 of methanesulfonyl chloride is introduced over 30 min. The stirring is continued for 20 h while gradually allowing it to climb back up to a temperature close to 20° C. 20 cm3 of a saturated aqueous solution of sodium hydrogen carbonate and 5 cm3 of water are added to the reaction mixture. Stirring is continued for 1 h at a temperature close to 20° C. The aqueous phase is extracted with 10 cm3 of dichloromethane. After decanting, the organic phase is dried over magnesium sulfate, filtered then concentrated using a rotary evaporator under reduced pressure (5 kPa). The crude product obtained is purified by trituration in 10 cm3 of hot diisopropyl ether. After filtering at a temperature close to 20° C., washing with 2 lots of 5 cm3 of diisopropyl ether and drying under vacuum, 0.6 g of methyl 7-[(methylsulfonyl)amino]-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate is obtained in the form of pink crystals.

Provenance & Evidence