1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Ethyl 3-[5-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl]propanoate

Participants

Reaction Conditions

Reaction Steps

3-Cyano-4-[(1-methylethyl)oxy]benzoic acid (can be prepared as described in WO2005/58848) (215 mg, 1.05 mmol), EDAC (219 mg, 1.14 mmol) and HOBt (156 mg, 1.14 mmol) in dry DMF (10 ml) were stirred at RT for 10 minutes. Added ethyl 3-{5-[(hydroxyamino)(imino)methyl]-1H-indol-1-yl}propanoate (D52) (288 mg, 1.05 mmol) and stirred for 1 hour at RT. Heated at 80° C. for 7 hours. The solution was cooled and EtOAc (50 ml) added. Washed with water (50 ml), sat. sodium hydrogen carbonate (50 ml) and water (50 ml). Dried over MgSO4 and evaporated off the solvent. The residue was crystallised from ether to yield 200 mg of the title compound as a very pale pink solid. MS (ES) C25H24N4O4 requires 444; found 445 (MH+)

Provenance & Evidence