C([O:3][CH2:4]CN1C2C=NC=CC=2N=C1CN1CCNCC1)C.Br[CH2:23][CH2:24][N:25]1[C:29](=[O:30])[N:28](CC)[N:27]=[N:26]1.[C:33](=[O:36])([O-:35])[O-].[Na+].[Na+].CN(C)C(=O)C>O>[C:4]([OH:3])(=[O:30])[C:33]([OH:35])=[O:36].[CH2:24]([N:25]1[C:29](=[O:30])[NH:28][N:27]=[N:26]1)[CH3:23]
A mixture of 2.7 parts of 3-(2-ethoxyethyl)-2-(1-piperazinylmethyl)3H-imidazo[4,5-c]pyridine, 2.7 parts of 1-(2-bromoethyl)-4-ethyl-1,4-dihydro-5H-tetrazol-5-one, 1.3 parts of sodium carbonate and 72 parts of N,N-dimethylacetamide was stirred overnight at 70° C. The reaction mixture was poured into water and the product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was converted into the ethanedioate salt in 2-propanol. The salt was filtered off and dried, yielding 3.9 parts (64.0%) of 1-[2-[4-[[3-(2-ethoxyethyl)-3H-imidazo[4,5-b]pyridin-2yl]methyl]-1-piperazinyl]ethyl)]-4-ethyl-1,4-dihydro-5H-tetrazol-5-one ethanedioate(1:2); mp. 179.0° C. (compound 38).
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