[OH:1][C:2]1[C:3]([C:17](=O)[CH3:18])=[CH:4][S:5][C:6]=1[C:7]1[CH:16]=[CH:15][C:14]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2[CH:8]=1.[NH:20]1[C:24]([C:25]2[CH:34]=[CH:33][C:28]([C:29]([NH:31][NH2:32])=[O:30])=[CH:27][CH:26]=2)=[N:23][N:22]=[N:21]1.Cl.O>CN(C)C=O>[OH:1][C:2]1[C:3]([C:17](=[N:32][NH:31][C:29](=[O:30])[C:28]2[CH:33]=[CH:34][C:25]([C:24]3[NH:23][N:22]=[N:21][N:20]=3)=[CH:26][CH:27]=2)[CH3:18])=[CH:4][S:5][C:6]=1[C:7]1[CH:16]=[CH:15][C:14]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2[CH:8]=121.6 mg (0.0793 mmol) of 1-[4-hydroxy-5-(5,6,7,8-tetrahydronaphthalen-2-yl)thiophen-3-yl]ethanone and 17.9 mg (0.0877 mmol) of 4-(1H-tetrazol-5-yl)benzohydrazide in N,N-dimethylformamide (1.0 ml) was stirred with a drop of concentrated hydrochloric acid at 60° C. for 3 hours. After completion of the reaction, water was added, and the precipitated solid was collected by filtration, washed with chloroform (2.0 ml) and dried under reduced pressure to obtain the desired product (0.7 mg, yield 2%).
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