Hydrochloric Acid → methyl 2-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)thiazole-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(benzo[d]thiazol-2-yl)-1,2,3,4-tetrahydroisoquinoline-8-carboxamide dihydrochloride (1B) (5.3 g, 13.86 mmol) and methyl 2-chlorothiazole-4-carboxylate (2.5 g, 14 mmol) in DMA (60 mL) was added Cs2CO3 (25 g, 70 mmol). The reaction mixture was stirred at 50° C. overnight. The reaction mixture was cooled to rt, acidified with 5% HCl, extracted with DCM, washed with water, brine, dried over Na2SO4, and concentrated under reduced pressure. The crude material was purified by column chromatography on silica gel eluting with 5% MeOH in DCM to provide 4.2 g (67%) of the desired product methyl 2-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)thiazole-4-carboxylate (1C): LC/MS (APCI): m/z 451.0 (M+H).

Provenance & Evidence