Trifluoroacetic acid → HCID 71499119, compound

Participants

Reaction Steps

To a stirred suspension of (RS)-3-{3-chloro-4-[3-(6-chloro-pyridin-3-yl)-ureido]-phenyl}-pyrrolidine-1-carboxylic acid tert-butyl ester (68 mg) in dichloromethane (6 ml) was added trifluoroacetic acid (92 μl) and the reaction mixture was then stirred at room temperature for 34 h. The reaction mixture was then poured into 1 M aq. NaOH and the resulting mixture was extracted twice with EtOAc. The organic layers were dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash column chromatography (Isolute® Flash-NH2 from Separtis); gradient: heptane/EtOAc/MeOH) to afford (RS)-1-(6-chloro-pyridin-3-yl)-3-(2-chloro-4-pyrrolidin-3-yl-phenyl)-urea (9 mg, 17%) as an off-white solid. MS (ISP): 355.1 ([{37Cl}M+H]+), 353.1 ([{37Cl35Cl}M+H]+), 351.2 ([{35Cl}M+H]+).

Provenance & Evidence