[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]2[S:12][C:11]([C:13]#[N:14])=[N:10][N:9]=2)[CH2:3][CH2:2]1.[F:15][C:16]1[CH:17]=[C:18]([CH:27]=[CH:28][C:29]=1[F:30])[CH2:19]N1CCC(N)CC1.C(N(C(C)C)CC)(C)C>C(#N)C.ClCCl>[F:15][C:16]1[CH:17]=[C:18]([CH:27]=[CH:28][C:29]=1[F:30])[CH2:19][N:1]1[CH2:2][CH2:3][CH:4]([NH:7][C:8]2[S:12][C:11]([C:13]#[N:14])=[N:10][N:9]=2)[CH2:5][CH2:6]1
A mixture of 5-chloro-[1,3,4]thiadiazole-2-carbonitrile (0.3 g, 2.06 mmol) (D6) (prepared by a procedure similar to that described in U.S. Pat. No. 5,736,545), 1-(3,4-difluoro-benzyl)-piperidin-4-ylamine (D7) (0.47 g, 2.06 mmol) and diisopropylethylamine (0.54 ml, 3.09 mmol) in acetonitrile (5 ml) in a sealed tube, was stirred at 80° C. for 1 h., under microwave irradiation. After this period, the reaction mixture was diluted with dichloromethane and extracted with a saturated solution of sodium carbonate (25 ml). The organic layer was separated, dried (Na2SO4) and the solvent evaporated in vacuo. The crude product was purified by short open column chromatography (silica gel; 0-2.5% ammonia in methanol (7M)/dichloromethane). The desired fractions were collected and evaporated in vacuo. The crude product was precipitated from acetonitrile to yield E19 (0.17 g, 25%) as a solid. C15H15F2N5S requires 335. Found 336 (MH+).
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