Hydrochloric Acid → N-[3-(1-cyclohexyl-4-hydroxy-2-oxo-4a,5,6,7,8,8a-hexahydroquinolin-3-yl)-1,1-dioxo-4H-1$l^{6},2,4-benzothiadiazin-7-yl]methanesulfonamide

Participants

Reaction Conditions

Reaction Steps

2-{Cyclohexyl-[2-(7-methanesulfonylamino-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)-acetyl]-amino}-cyclohexanecarboxylic acid ethyl ester (0.48 g, 0.845 mmol) was dissolved in ethanol (15 mL), a 21% w/w solution of sodium ethoxide in ethanol (1.095 g, 3.38 mmol) was added. The mixture was stirred at 60° C. for 4 h and allowed to cool to 25° C. The mixture was poured into a 1.0 M aqueous hydrochloric acid solution (50 mL). The product started to precipitate and was collected by vacuum filtration. The precipitate was washed with water and dried under high vacuum to afford the pure product, N-[3-(1-cyclohexyl-4-hydroxy-2-oxo-1,2,4a,5,6,7,8,8a-octahydro-quinolin-3-yl)-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl]-methanesulfonamide (0.183 g, 0.35 mmol, 41.4%), as a tan solid. 1H NMR (400 MHz, DMSO-d6) δ: 1.07-1.89 (18H, m), 2.32 (1H, bs), 3.05 (3H, s), 3.61-4.33 (3H, m), 7.47-7.60 (3H, m), 7.49-7.57 (3H, m), 10.15 (1H, s), 13.88 (1H, s). LC-MS (ESI) calcd for C23H30N4O6S2 522.16, found 523.4 [M+H+].

Provenance & Evidence