[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:12][C:11]([C:13](Cl)=[O:14])=[CH:10][CH:9]=1.[NH2:16][C:17]1[O:18][C:19]([C:22]2[O:23][CH:24]=[CH:25][CH:26]=2)=[N:20][N:21]=1.CO>N1C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:12][C:11]([C:13]([NH:16][C:17]2[O:18][C:19]([C:22]3[O:23][CH:24]=[CH:25][CH:26]=3)=[N:20][N:21]=2)=[O:14])=[CH:10][CH:9]=1Commercially available 5-(2-fluorophenyl)-2-furancarbonyl chloride (93 mg, 0.41 mmol) was added to a solution of commercially available 2-amino-5-(2-furyl)-1,3,4-oxadiazole (50 mg, 0.33 mmol) in pyridine (1.3 mL) under ice-cooling, followed by stirring at room temperature for 2.5 hr and then at 60° C. for 2 hr. Methanol was added to the reaction solution. The solvent was distilled off, and water was added to the residue. The precipitated crystals were collected by filtration, washed with water, methanol, and ethyl acetate sequentially, and then dried to obtain the title compound (77 mg, 0.23 mmol) (yield: 70%).
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