[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]1[O:11][N:10]=[C:9]([NH2:12])[N:8]=1.C(N[C:16]([C:18]1S[CH:20]=[CH:21][C:22]=1[Cl:23])=O)#N.Cl.NO.O.N1C=CC=[CH:30][CH:29]=1>>[Cl:23][C:22]1[CH:21]=[CH:20][C:29]([CH:30]=[N:12][C:9]2[N:8]=[C:7]([C:3]3[S:4][CH:5]=[CH:6][C:2]=3[Cl:1])[O:11][N:10]=2)=[CH:16][CH:18]=15-(3-Chloro-thiophen-2-yl)-[1,2,4]-oxadiazol-3-ylamine: A solution of N-cyano-3-chloro-thiophene-2-carboxylic acid amide (467.5 mg, 2.5 mmol), hydroxylamine hydrochloride (174 mg, 2.5 mmol) in pyridine (5 mL) was heated at 100° C. for 8 h. It was cooled and poured into water (80 mL), and the mixture was extracted with ethyl acetate (3×20 mL). The combined organic layer was washed with water, 1N HCl, dried with Na2SO4, and concentrated. The crude residue was purified by column chromatography (hexane:ethyl acetate, 10:1) to yield 189 mg (37%) of title compound. 1H NMR (CDCl3): 7.56 (d, J=5.4 Hz, 1H), 7.09 (d, J=5.4 Hz, 1H), 4.49 (brs, 2H).
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