C([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[S:16][C:17]([C:20]([F:23])([F:22])[F:21])=[N:18][N:19]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.C(N(C(C)C)CC)(C)C.ClC(OC(Cl)C)=O>ClCCl>[NH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[S:16][C:17]([C:20]([F:23])([F:21])[F:22])=[N:18][N:19]=2)[CH2:10][CH2:9]1To a stirred solution of (1-benzyl-piperidin-4-yl)-(5-trifluoromethyl-[1,3,4]thiadiazol-2-yl)-amine (D3) (0.50 g, 1.46 mmol) and diisopropylethylamine (0.76 ml, 4.38 mmol) in dichloromethane (20 ml) at 0° C., was added 1-chloroethyl chloroformate (0.47 ml, 4.38 mmol). The reaction mixture was stirred at room temperature for 2 h. and after this period, the solvent evaporated in vacuo. The crude product was dissolved in methanol (30 ml) and the reaction mixture was stirred at reflux for 1.5 h. After evaporation of the solvent, the crude product was dissolved in water and extracted with diethyl ether (2×25 ml) and dichloromethane (3×25 ml). The aqueous layer was separated and evaporated in vacuo. The crude product was purified by reverse phase HPLC. The desired fractions were collected and evaporated in vacuo to yield D4 (0.29 g, 79%) as a solid. C8H11F3N4S requires 252. Found 253 (MH+).
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