1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-[4-(5-{3-Chloro-4-[(trifluoromethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl]propanoic acid

Beteiligte Stoffe

Reaktionsschritte

3-Chloro-4-[(trifluoromethyl)oxy]benzoic acid (commercial source) (131 mg), EDCI (114 mg) and HOBT (81 mg) were dissolved in DMF (2.5 ml) and stirred at RT for 10 minutes. Ethyl 3-{5-[(hydroxyamino)(imino)methyl]-1H-indol-1-yl}propanoate (D57) (150 mg) in DMF (2.5 ml) was added and stirring continued at RT for 2 hours. The mixture was then heated at 80° C. overnight. The reaction mixture was evaporated to dryness then extracted with EtOAc (2×25 ml) from H2O (25 ml). The combined organic solutions were evaporated to dryness and the residue treated with EtOH and 2 M aq. NaOH (1:1 mixture, 20 ml). This mixture was stirred at 50° C. for 2 hours then evaporated to remove the EtOH. The resultant precipitate was filtered off and washed with a mixture of H2O and EtOH then 2 M HCl. The residue was recrystallised from hot EtOH to give the title compound (62 mg) as a white solid. δH (d6-DMSO, 400 MHz): 2.81 (2H, t), 4.50 (2H, t), 7.08 (1H, d), 7.36 (1H, apparent t), 7.61 (1H, d), 7.83 (1H, d), 7.89 (1H, d), 7.96 (1H, d), 8.32 (1H, dd), 8.50 (1H, d). MS (ES−): C20H1335CIF3N3O4 requires 451; found 450 (M−H+).

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