[H-].[Na+].[OH:3][CH2:4][CH2:5][CH2:6][S:7]([NH2:10])(=[O:9])=[O:8].Cl[C:12]1[CH:13]=[CH:14][C:15]2[N:16]([N:18]=[CH:19][N:20]=2)[N:17]=1.Cl.[Cl-].[Na+]>CN(C)C=O>[S:7]([CH2:6][CH2:5][CH2:4][O:3][C:12]1[CH:13]=[CH:14][C:15]2[N:16]([N:18]=[CH:19][N:20]=2)[N:17]=1)(=[O:9])(=[O:8])[NH2:10]In 12 ml of dimethylformamide was suspended 0.48 g of 60% sodium hydride in oil followed by addition of 0.835 g of 3-hydroxy-1-propanesulfonamide and the mixture was stirred under reduced pressure at room temperature for 30 minutes. Then, 0.928 g of 6-chloro[1,2,4]triazolo[1,5-b]pyridazine was added and the mixture was further stirred at room temperature for 18 hours. Following addition of 40 ml of ice water, the reaction mixture was adjusted to pH6 with 1N-hydrochloric acid then saturated with sodium chloride. The aqueous layer was extracted with tetrahydrofuran and the extract was dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was crystallized from ethyl ether. The washed crystals were recrystallized from hot methanol to provide 0.811 g of title compound. m.p. 145°-147° C.
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