Benzamidine → HCID 131722461, compound

Participants

Reaction Steps

6-Cyanobenzoxazolinone (5.0 mmol, 0.80 g) was synthesized as previously described and added to a solution of 3-[1,1′]-biphenyl-1,2-propen-3-one (5.0 mmol, 1.04 g) and triethylamine (10.00 mmol, 1.39 mL) in 40 mL acetonitrile. The reaction mixture was warmed from ambient temperature to 77° C. for 2h. The reaction mixture was concentrated and placed under high vaccum to give the crude product. The crude material was used directly. LRMS: m/z 386 (M+NH4,100). The 1N-[[1,1′]-biphenylcarbonyl]ethyl-6-cyanobenzoxazolinone was converted to its corresponding benzamidine via the Pinner synthesis and amidination with ammonium carbonate to give crude 1N-[4-biphenylcarbonyl]ethyl-6-amidinobenzoxazolinone. The crude product was purified by standard reverse phase HPLC. LRMS: m/z 386(M+H,100). HRMS: calcd for C23H20N3O3, 386.150467; found, 386.150040.

Provenance & Evidence