1,1-Bis(methylthio)-2-nitroethylene → 1-[[(3S)-Hexahydro-3-[[2-nitro-1-[[4-(trifluoromethoxy)phenyl]amino]ethenyl]amino]-2-oxo-1H-azepin-1-yl]acetyl]pyrrolidine

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(trifluoromethoxy)aniline (20 mg, 0.11 mmol) and 1,1-bis(methylthio)-2-nitroethylene (19 mg, 0.12 mmol) in ethanol (0.25 mL) was heated at 80° C. for 5 h. To the mixture was added 1-[[(3S)-3-aminohexahydro-2-oxo-1H-azepin-1-yl]acetyl]pyrrolidine (27 mg, 0.11 mmol). The resulting solution was stirred at 80° C. for 14 h, and the mixture was then concentrated in vacuo. The residue was purified by preparative HPLC (YMC-PACK ODSA S5 (30×250 mm); flow rate 25 mL/min; gradient time 55 min) to furnish the title compound as a white solid (30 mg, 55%): MS (ESI, pos. ion spectrum) m/z 486; HPLC (method A) tR 3.59 min.

Provenance & Evidence