[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:11][CH2:12][C:13]1[CH:22]=[CH:21][C:16]([C:17]([NH:19][OH:20])=[NH:18])=[CH:15][CH:14]=1.N1C=CC=CC=1.[C:33]1([O:39]C(Cl)=O)C=CC=CC=1.N12CCCN=C1CCCCC2>ClCCl.C(#N)C>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:11][CH2:12][C:13]1[CH:22]=[CH:21][C:16]([C:17]2[NH:18][C:33](=[O:39])[O:20][N:19]=2)=[CH:15][CH:14]=1280 mg 4-[2-(Benzooxazol-2-yl-butyl-amino)-ethyl]-N-hydroxy-benzamidine were dissolved in 5 ml dichloromethane. 78 μl pyridine and 120 μl phenylchloroformate were added and the mixture stirred at room temperature for ten minutes. The mixture was diluted by the addition of 15 ml acetonitrile and 115 μl ml 1,8-Diazabicyclo[5.4.0]undec-7-ene were added. The mixture was stirred at room temperature for 10 minutes. The mixture was evaporated in vacuo and the resulting crude material was purified by reversed phase HPLC to obtain 105 mg 3-{4-[2-(Benzooxazol-2-yl-butyl-amino)-ethyl]-phenyl}-4H-[1,2,4]oxadiazol-5-one as an amorphous lyophilisate.
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