[C:1](O)(=O)[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[OH:17][NH:18][C:19]([C:21]1[C:22]2[CH:23]=[CH:24][C:25]([NH:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[O:39][CH3:40])=[N:26][C:27]=2[CH:28]=[CH:29][CH:30]=1)=[NH:20]>C1COCC1>[CH3:40][O:39][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=1[CH2:32][NH:31][C:25]1[CH:24]=[CH:23][C:22]2[C:27](=[CH:28][CH:29]=[CH:30][C:21]=2[C:19]2[N:20]=[C:1]([CH3:2])[O:17][N:18]=2)[N:26]=1To a stirred solution of acetic acid (48 mg, 0.8 mmol) in THF (7.5 ml) was added at room temperature 1,1′-carbonyl-diimidazole (151 mg, 0.93 mmol). The mixture was allowed to stir for 15 min at room temperature and for 90 min at 70° C., cooled to room temperature and N-hydroxy-2-(2-methoxy-benzylamino)-quinoline-5-carboxamidine (200 mg, 0.62 mmol) was added. The reaction mixture was allowed to stir at room temperature for 30 min, evaporated to dryness and diluted with acetic acid (7.5 ml). The reaction mixture was allowed to stir for 2 h at 100° C., evaporated, poured into saturated NaHCO3 solution (20 ml) and extracted with ethyl acetate (2×30 ml). The combined organic layers were washed with brine (20 ml), dried (MgSO4) and evaporated. The crude product was purified by flash chromatography (ethyl acetate/heptane) on silica gel and crystallization (dichloromethane/hexane) to yield the title compound as white solid (108 mg, 50%).
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