1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3,5-Dimethoxy-4-methyl-N-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)-2-nitro-benzyl]-benzamide

Participants

Reaction Steps

A suspension of compound 1e (3.34 g, 14.3 mmol), 3,5-dimethoxy-4-methylbenzoic acid (4.2 g, 21.4 mmol), EDCI (4.1 g, 21.4 mmol), and HOAt (190 mg, 1.4 mmol) in a mixture of dichloromethane (60 mL) and DMF (30 mL) was stirred at rt for 12 h. The reaction mixture was diluted with ethyl acetate and washed with 1 N HCl. The solid which precipitated was recovered by filtration. The ethyl acetate layer was washed with saturated NaHCO3 solution and brine, dried Na2SO4, and concentrated on a rotary evaporator. The residue was recrystallized (ethyl acetate/hexane/petroleum ether) and combined with the filtered solid to afford compound 1f (5.55 g, 94%) as a cream colored solid. ESI-MS m/e 413.2 (M+1).

Provenance & Evidence