Citric Acid → HCID 89815259, compound

Participants

Reaction Steps

A solution of 1,2,4-thiadiazol-5-amine (0.740 g, 7.31 mmol) and triethylamine (3.06 ml, 21.94 mmol) in 20 mL DCM was cooled to −78° C. and was treated with sulfuryl chloride (0.595 ml, 7.31 mmol). The cooling bath was removed, and the reaction mixture was allowed to stir for 20 minutes. LC/MS showed mostly desired intermediate, so 5-chloro-1,2,3,4-tetrahydro-2,6-naphthyridine hydrochloride (Anichem, North Brunswick, N.J., 0.750 g, 3.66 mmol) was added and the reaction mixture was allowed to stir for one hour. The reaction mixture was then poured into 1N citric acid and was extracted with EtOAc. The organics were concentrated. Purification of the resulting residue by silica gel column chromatography (0 to 100% EtOAc/heptane) gave 5-chloro-N-(1,2,4-thiadiazol-5-yl)-3,4-dihydro-2,6-naphthyridine-2(1H)-sulfonamide (1.064 g, 3.21 mmol). [M+H]+=332.1

Provenance & Evidence