ClC1N=NC([CH:8]2[CH2:14][NH:13][CH:12]3[CH2:15][CH2:16][N:9]2[CH2:10][CH2:11]3)=CC=1.[C:17]1([SH:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[C:24](=[O:27])([O-:26])[O-].[Cs+].[Cs+].[OH-:30].[Na+].C[N:33]([CH:35]=[O:36])C>>[C:35]([OH:36])(=[O:30])/[CH:15]=[CH:16]/[C:24]([OH:26])=[O:27].[C:17]1([S:23][C:35]2[N:33]=[N:9][C:10]([N:13]3[CH:12]4[CH2:11][CH2:10][N:9]([CH2:16][CH2:15]4)[CH2:8][CH2:14]3)=[CH:11][CH:12]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1A mixture of 4-(6-chloropyridazin-3-yl-1,4-diazabicyclo[3.2.2]nonane (0.27 g; 1.1 mmol) thiophenol (0.96 g; 8.4 mmol), caesium carbonate (369 mg; 1.1 mmol) and DMF (1 ml) was stirred at 125° C. for 15 hours. Aqueous sodium hydroxide (5 ml; 4M) was added. The mixture was extracted with dichloromethane (3×5 ml). Chromatography on silica gel with dichloromethane, 10% methanol and 1% aqueous ammonia as solvent gave the title compound as an oil. Yield 0.32 g (93%). The corresponding salt was obtained by addition of a diethyl ether and methanol mixture (9:1) saturated with fumaric acid. Mp. 102.2° C.
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