[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=2)[CH2:11][CH2:10]1.N[NH:24][C:25]([NH2:27])=[S:26].O.[OH-].[Na+]>C1(C)C=CC=CC=1.FC(F)(F)C(O)=O.C1COCC1.CO.C(OCC)(=O)C>[NH2:27][C:25]1[S:26][C:21]([C:18]2[CH:19]=[CH:20][C:15]([N:12]3[CH2:13][CH2:14][CH:9]([O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1])[CH2:10][CH2:11]3)=[CH:16][CH:17]=2)=[N:22][N:24]=1A solution of 4-(5-methoxypentyloxy)-N-(4-cyanophenyl)piperidine (294 mg) and thiosemicarbazide (0.68 g) in toluene (20 ml) and trifluoroacetic acid (10 ml) was stirred at 60-65° C. for 7 hours. After cooling, the reaction mixture was poured into a mixture of water (100 ml) and ethyl acetate (200 ml) and adjusted to pH 10 with 1N-sodium hydroxide. The mixture was dissolved in a mixture of THF (50 ml) and methanol (10 ml). The organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated in vacuo. The resulting precipitate was washed with isopropyl ether and dried in vacuo to give 2-amino-5-[4-[4-(5-methoxypentyloxy)-piperidin-1-yl]phenyl]-1,3,4-thiadiazole (1.29 g).
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