1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 5-[3-(1H-indol-4-yl)-1,2,4-oxadiazol-5-yl]-2-[(1-methylethyl)oxy]benzonitrile

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Reaction Conditions

Reaction Steps

To 3-cyano-4-[(1-methylethyl)oxy]benzoic acid (can be prepared as described in WO2005/58848) (500 mg, 2.44 mmol) in DMF (15 ml) was added EDAC (514 mg, 2.67 mmol) and HOBt (367 mg, 2.67 mmol) and the solution left standing for 30 minutes. Added N-hydroxy-1H-indole-4-carboximidamide (D9) (427 mg, 2.44 mmol) and left standing for 1 hour. To the solution were added EDAC (117 mg, 0.61 mmol) and HOBt (84 mg, 0.61 mmol) and left standing for 2 hours. To the solution were added EDAC (234.9 mg, 1.22 mmol) and HOBt (167.7 mg, 1.22 mmol) and left standing overnight. Heated at 80° C. overnight, cooled and added EtOAc (30 ml). Washed with water (30 ml), sat. sodium hydrogen carbonate (30 ml) and water (30 ml). Dried over MgSO4 and evaporated off the solvent. The residue was triturated with diethyl ether to give 353 mg of the title compound as a pale brown solid. δH (400 MHz, d6-DMSO) 1.39 (6H, d), 4.94-5.03 (1H, m), 7.09-7.10 (1H, m), 7.30 (1H, t), 7.56-7.59 (2H, m), 7.67 (1H, d), 7.92 (1H, dd), 8.45 (1H, dd), 8.55 (1H, d), 11.52 (1H, broad s). MS (ES) C20H16N4O2 requires 344; found 345 (MH+).

Provenance & Evidence