[CH:1]1([N:7]2[CH2:12][CH2:11][CH:10]([C:13]3[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=3)[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N[NH:22][C:23]([NH2:25])=[S:24].[F:26][C:27]([F:32])([F:31])[C:28]([OH:30])=[O:29]>C1(C)C=CC=CC=1>[F:26][C:27]([F:32])([F:31])[C:28]([OH:30])=[O:29].[CH:1]1([N:7]2[CH2:8][CH2:9][CH:10]([C:13]3[CH:14]=[CH:15][C:16]([C:17]4[S:24][C:23]([NH2:25])=[N:22][N:18]=4)=[CH:19][CH:20]=3)[CH2:11][CH2:12]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1A mixture of 4-(1-cyclohexyl-4-piperidyl)benzonitrile (0.68 g), thiosemicarbazide (0.58 g) and trifluoroacetic acid (3.5 ml) in toluene (7 ml) was stirred for 7 hours at 70° C. After being cooled to room temperature, the solvent was evaporated in vacuo. Then the residue was dissolved in tetrahydrofuran and poured into water. The solution was adjusted to pH 8 with 1N aqueous sodium hydroxide. The resulting precipitate was collected by filtration and washed with water and isopropyl ether to give 5-[4-(1-cyclohexyl-4-piperidyl)phenyl]-1,3,4-thiadiazol-2-amine trifluroacetate (0.80 g).
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