Citric Acid → HCID 89815303, compound

Participants

Reaction Conditions

Reaction Steps

A solution of imidazole (1.530 g, 22.47 mmol) and thiazol-2-amine (0.750 g, 7.49 mmol) in 8 mL DCM was cooled to −78° C. and was treated with sulfuryl chloride (0.609 ml, 7.49 mmol). After stirring for 20 minutes, the cooling bath was removed and the reaction mixture was allowed to stir for an additional 30 minutes. 5-Bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride (ASW Medchem, Brunswick, N.J., 1.396 g, 5.62 mmol) was added, followed by triethylamine (7.31 ml, 52.4 mmol). The reaction mixture was then heated to 80° C. for 30 minutes. The mixture was cooled to rt and poured into 1N citric acid solution before being extracted into EtOAc. The organics were dried over MgSO4 and concentrated. Purification of the residue by silica gel column chromatography (0 to 100% EtOAc/heptane) gave 5-bromo-N-(thiazol-2-yl)-3,4-dihydroisoquinoline-2(1H)-sulfonamide (1.092 g, 2.92 mmol). [M+H]+=375.6.

Provenance & Evidence