Hydrochloric Acid → HCID 46832785, compound

Participants

Reaction Steps

To a stirred solution of 2,2-difluoro-3-[3-(2-fluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]-N-methylpropanamide (ca. 1 mmol) at 0° C., was added borane-tetrahydrofuran complex (1 M in THF, 3 mL, 3 mmol). After stirring for 2 h, the mixture was quenched with dilute hydrochloric acid, basified (2 N NaOH) and extracted with ethylacetate. The organic layer was washed with water, dried (MgSO4) and evaporated. The residue was purified by silica gel column chromatography (hexanes: ethylacetate, gradient elution) to afford the crude product which was further purified by reverse phase hplc (Xterra RP18 19×150 mm, 5 u, 55% MeOH 45% H2O w/0.05% NH4OH, 20 mL/min). The residue obtained was dissolved in diethyl ether, treated with excess ethereal HCl and lyophilized to afford 2,2-difluoro-3-[3-(2-fluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]-N-methylpropan-1-amine hydrochloride as a white solid.

Provenance & Evidence