Dimethylsulphamoyl chloride → HCID 10202483, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-(4-amino-phenyl)-3-cyclopentyl-N-thiazol-2-yl-propionamide (prepared in Example 3, 105 mg, 0.33 mmol) in pyridine (5 mL) was treated with dimethylsulfamoyl chloride (0.04 mL, 0.38 mmol). The reaction mixture was stirred at 25° C. for 24 h. At this time, the reaction was concentrated in vacuo. The residue was dissolved in methylene chloride, and the organic phase was washed with a 1N aqueous hydrochloric acid solution, a saturated aqueous sodium bicarbonate solution, and a saturated aqueous sodium chloride solution. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. High pressure liquid chromatography (Chromegasphere SI-60, 10 μM, 60 Å, 25 cm×23 cm ID, 60/40 heptane/ethyl acetate) afforded the N-{4-[2-cyclopentyl-1-(thiazol-2-ylcarbamoyl)-ethyl]-phenyl}-dimethylsulfamide (21.3%) as a white solid: mp 110-112° C.; FAB-HRMS m/e calcd for C19H26N4O3S2 (M+H)+ 423.1524, found 423.1524.

Provenance & Evidence