[CH3:1][C:2]1[N:3]=[C:4]([NH:14][C:15]([NH2:17])=[S:16])[S:5][C:6]=1[C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][N:8]=1.[ClH:18].[C:19](OCC)(=O)[CH3:20]>CN(C)C=O.O1CCOCC1.ICC>[ClH:18].[ClH:18].[CH3:1][C:2]1[N:3]=[C:4]([NH:14][C:15](=[NH:17])[S:16][CH2:19][CH3:20])[S:5][C:6]=1[C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][N:8]=1To a suspension of N-(4-methyl-5-(4-methylpyridin-2-yl)thiazol-2-yl)thiourea (529 mg) in N,N-dimethylformamide (10 ml) were added a solution of hydrogen chloride in 1,4-dioxane (4N, 1 ml) and iodoethane (0.8 ml), and the mixture was stirred at 70° C. for 4 hours. Ethyl acetate (100 ml) was added to the mixture, and the mixture was cooled. The precipitate was collected by filtration and purified by column chromatography (silica gel, triethylamine:methanol:dichloromethane=1:2:100). The combined fractions were evaporated under reduced pressure, and the residue was dissolved in ethyl acetate (5 ml). To the solution was added a solution of hydrogen chloride in 1,4-dioxane (4N, 1.25 ml). The precipitate was collected by filtration and dried under reduced pressure to give N-(4-methyl-5-(4-methylpyridin-2-yl)thiazol-2-yl)-S-ethylisothiourea dihydrochloride (0.69 g).
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