Hydrochloric Acid → 2-{Cyclohexyl-[2-(7-methanesulfonylamino-1,1-dioxo-1,4-dihydro-1lambda6-benzo[1,2,4]thiadiazin-3-yl)-acetyl]-amino}-cyclohexanecarboxylic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

(7-Methanesulfonylamino-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)-acetic acid (prepared as described in Example 1j, 0.333 g, 1.0 mmol) was dissolved in anhydrous N,N-dimethylformamide (5 mL). 2-Cyclohexylamino-cyclohexanecarboxylic acid ethyl ester (0.253 g, 1.0 mmol) was added followed by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.201 g, 1.05 mmol). Then N-methylmorpholine (212 mg, 2.1 mmol) was added. The mixture was stirred at 25° C. for 5 h. The solution was poured into 1.0 M aqueous hydrochloric acid solution (100 mL). The aqueous layer was extracted with ethyl acetate (2×100 mL). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to afford the crude product, 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, 84.5%), as a yellow oil. LC-MS (ESI) calcd for C25H36N4O7S2 568.20, found 569.3 [M+H+].

Provenance & Evidence