Hydrochloric Acid → HCID 117736975, compound

Participants

Reaction Conditions

Reaction Steps

A 100-mL RBF was charged with perfluorophenyl 1-(5,6-dichloro-2-methoxypyridin-3-yl)-2-oxo-1,2-dihydroquinoline-6-sulfonate (3.0 g, 5.29 mmol) then purged with nitrogen. THF (191 mL) and 3-aminoisoxazole (4.89 g, 5.82 mmol) were introduced and the resultant tan solution cooled to 0° C. A solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (1.0 M, 11.1 mL, 11.1 mmol) was added dropwise via syringe to the stirred reaction mixture over 5 min. After 15 min, 1.0 N HCl (25 mL) was introduced and the resultant reaction mixture was allowed to warm to RT. The mixture was diluted with and EtOAc (25 mL) and the layers were separated, and the aqueous layer was further extracted with EtOAc (3×25 mL). The combined organic layers were then washed with brine (100 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was then purified by flash column chromatography (100-g Biotage column, eluent: gradient, 0 to 100% EtOAc in heptane with 10% CH2Cl2 as an additive) to afford 1-(5,6-dichloro-2-methoxypyridin-3-yl)-N-(isoxazol-3-yl)-2-oxo-1,2-dihydroquinoline-6-sulfonamide (1.97 g, 4.22 mmol, 80% yield) as a white amorphous solid. 1H NMR (400 MHz, DMSO-d6) δ=8.62 (d, J=2.3 Hz, 1H), 8.47 (s, 1H), 8.28 (d, J=9.6 Hz, 1H), 7.94 (dd, J=2.3, 9.1 Hz, 1H), 7.19 (d, J=9.0 Hz, 1H), 6.91 (d, J=9.7 Hz, 1H), 3.82 (s, 3H). m/z (ESI) 468.9 (M+H)+.

Provenance & Evidence