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

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Reaction Steps

The 3-cyano-4-[(1-methylethyl)oxy]benzoic acid (can be prepared as described in WO2005/58848) (113 mg, 0.55 mmol), EDAC (115 mg, 0.60 mmol) and HOBt (82 mg, 0.60 mmol) were dissolved in DMF (5 ml) and left standing for 15 minutes. Added ethyl 3-{4-[(hydroxyamino)(imino)methyl]-1H-indol-1-yl}propanoate (D57) (150 mg, 0.55 mmol) and stood overnight at RT. Heated solution at 80° C. for 2 hours. LC/MS showed mostly product. After heating for a few more hours there was no change. Added EtOAc (20 ml) and washed with water (30 ml). Washed with saturated sodium hydrogen carbonate (30 ml) and water (2×30 ml). Dried over MgSO4 and evaporated off the solvent to obtain 81 mg of the title compound as a pale brown solid. MS (ES) C25H44N4O4 requires 444; found 445 (MH+).

Provenance & Evidence