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

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-cyano-4-[(1-methylethyl)oxy]benzoic acid (can be prepared as described in WO2005/58848) (371 mg, 1.81 mmol), EDAC (547 mg, 2.85 mmol) and HOBt (437 mg, 2.85 mmol) in DMF (5 ml) was left standing at RT for 10 minutes. Added ethyl 3-{5-[(hydroxyamino)(imino)methyl]-1H-indazol-1-yl}propanoate (D52) (500 mg, 1.81 mmol) and left standing overnight at RT. Added EDAC (200 mg, 1.04 mmol) and left standing for 24 hours. The mixture was heated at 80° C. for 2 days, standing at RT each night. The mixture was heated at 80° C. for a further 4 hours. Added EtOAc (50 ml) and washed with water (60 ml), sat. NaHCO3 (60 ml) and water (60 ml). The EtOAc layer was dried (MgSO4) and the solvent evaporated. Triturating with ethanol gave the title compound (523 mg) as a beige solid. MS (ES): C24H23N5O4 requires 445; found (MH+) 446.

Provenance & Evidence