N-methyl-2-pyrrolidone → HCID 117629594, compound

Participants

Reaction Steps

To round bottom flask was added (R)-5-chloro-2-oxo-3-(1-(2-(1,2,3,6-tetrahydropyridin-4-yl)phenyl)ethyl)-N-(1,2,4-thiadiazol-5-yl)-2,3-dihydrobenzo[d]oxazole-6-sulfonamide hydrochloride (34-6) (10 mg, 0.018 mmol), followed by NMP (1 ml), then DIPEA (50 μl, 0.286 mmol), followed by METHANESULFONYL CHLORIDE (6.80 μl, 0.087 mmol). The reaction mixture was then capped (not under N2) & stirred at room temperature. Followed by LC/MS. After 2 minutes; the reaction mixture was diluted with H2O, then MeOH, & purified (without workup) by reverse phase chromatography (5-75% MeCN/H2O; 0.1% TFA in AQ; 20 min gradient; Waters 30×150 mm Sunfire 5 micron C18 column); desired fractions concentrated (GENEVAC), then dissolved in MeOH/DCM & concentrated to yield (R)-5-chloro-2-oxo-3-(1-(2-(1,2,3,6-tetrahydropyridin-4-yl)phenyl)ethyl)-N-(1,2,4-thiadiazol-5-yl)-2,3-dihydrobenzo-[d]oxazole-6-sulfonamide hydrochloride (36-1). MS [M+H] calculated; 596.1 observed; 596.0. 1H NMR (499 MHz, DMSO): δ 8.47 (s, 1H); 7.94 (s, 1H); 7.73 (d, J=7.8 Hz, 1H); 7.37 (d, J=7.6 Hz, 2H); 7.13 (d, J=9.8 Hz, 2H); 5.77-5.73 (m, 2H); 5.46 (s, 1H); 3.75-3.51 (m, 3H); 3.04-2.95 (m, 1H); 2.89 (s, 3H); 1.89-1.74 (m, 4H). Note: Peaks overlapping with water or solvent can not be accurately accounted for.

Provenance & Evidence