Hydrochloric Acid → HCID 57671235, compound

Participants

Reaction Conditions

Reaction Steps

2-(4-Fluoro-benzylamino)-cyclopentanecarboxylic acid ethyl ester (prepared as described in Example 11, 133.5 mg, 0.503 mmol) was mixed with (1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)-acetic acid (132.9 mg, 0.554 mmol) in N,N-dimethylformamide (4.6 mL). N-methylmorpholine (122 μL, 1.11 mmol) was added followed by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (106.2 mg, 0.554 mmol). The reaction mixture was shaken at 25° C. for 16 h. A 1.0 M aqueous hydrochloric acid solution (4.6 mL) was added at 25° C., and the aqueous layer was extracted with ethyl acetate (3×15 mL). The combined organic layers were washed with saturated aqueous brine solution (10 mL). The organic layer was dried over sodium sulfate, filtered, concentrated and dried in vacuo to afford the crude product, 2-[[2-(1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)-acetyl]-(4-fluoro-benzyl)-amino]-cyclopentanecarboxylic acid ethyl ester, as a pale yellow oil, which was directly used in the next step without further purification. LC-MS (ESI) calcd for C24H26FN3O5S 487.16, found 488.3 [M+H+].

Provenance & Evidence