[OH:1][CH:2]([CH2:10][OH:11])[CH2:3][N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.[CH2:12]([O:14][C:15]([C:17]1[CH:22]=[CH:21][N:20]=[N:19][C:18]=1Cl)=[O:16])[CH3:13]>O1CCOCC1>[CH2:12]([O:14][C:15]([C:17]1[CH:22]=[CH:21][N:20]=[N:19][C:18]=1[N:7]1[CH2:8][CH2:9][N:4]([CH2:3][CH:2]([OH:1])[CH2:10][OH:11])[CH2:5][CH2:6]1)=[O:16])[CH3:13]Grams 10.2 of 1-(2,3-dihydroxypropyl)piperazine and 5.9 g of 3-chloropyridazine-4-carboxylic acid ethyl ester in 100 ml dioxane were refluxed for one hour. Then it was settled, the solvent evaporated till dryness, and the residue dissolved in chloroform and washed with a small amount of water. The organic phase was made anhydrous, evaporated to dryness and the residue, purified on a column eluting with chloroform:methanol (9:1), gave 2.4 g of 3-[4-(2,3-dihydroxypropyl)piperazin-1-yl]pyridazine-4-carboxylic acid ethyl ester as an oil.
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