Hydrochloric Acid → 5-(5-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indazole

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Reaction Steps

3-chloro-4-[(1-methylethyl)oxy]benzoic acid (D3) (712 mg), EDCl.HCl (699 mg) and HOBT (493 mg) were dissolved in DMF (16.5 ml) and stirred at RT for 10 minutes. N-hydroxy-1H-indazole-5-carboximidamide (D2) (584 mg) was added and the mixture heated to 80° C. for 12 hours. The reaction mixture was then cooled to RT and left to stand for the weekend, evaporated to dryness and re-dissolved in H2O. This solution was extracted with EtOAc (×3) and the combined extracts washed with brine, evaporated and triturated with DCM twice, sonicated for 4 mins before filtering, drying and repeating once to give the title compound (407 mg) as a pink solid. δH (d6-DMSO, 400 MHz): 1.37 (6H, d), 4.89 (1H, septet), 7.46 (1H, d), 7.73 (1H, d), 8.04 (1H, d), 8.13 (1H, d), 8.20 (1H, s), 8.28 (1H, s), 8.58 (1H, s). MS (ES): C18H15ClN4O2 requires 354; found 355 (M+H).

Provenance & Evidence