1,1-Bis(methylthio)-2-nitroethylene → 1-[[(3S)-Hexahydro-3-[[1-[(2-methyl-6-benzofuranyl)amino]-2-nitroethenyl]amino]-2-oxo-1H-azepin-1-yl]acetyl]pyrrolidine

Participants

Reaction Steps

Preparation of title compound. To 2-methyl-6-benzofuranamine (30 mg, 0.16 mmol) in ethyl acetate (1 ML) was added 1,1-bis(methylthio)-2-nitroethylene (26 mg, 0.16 mmol) and the mixture heated at reflux for 30 minutes. After cooling to room temperature, 1-[[(3S)-3-aminohexahydro-2-oxo-1H-azepin-1-yl]acetyl]pyrrolidine (38 mg, 0.16 mmol) was added and the resultant mixture heated for an additional 2 h. The reaction mixture was placed directly on a silica column and the product was eluted with 2% methanol/chloroform. Product-containing fractions were concentrated in vacuo and the residue was then further purified by elution through a reverse-phase cartride (Varian C-18 Mega Bond Elut) with a gradient of 100% water to 100% methanol. Concentration of product-containing fractions in vacuo provided the title compound (9 mg, 12%): MS (ESI, pos. ion spectrum) m/z 456 (M+H); HPLC (method C) tR 3.5 min.

Provenance & Evidence