[Cl:1][C:2]1[S:3][C:4]([Cl:19])=[CH:5][C:6]=1[CH:7]1[CH2:16][C:15]2[N:14]=[CH:13][CH:12]=[C:11]([CH3:17])[C:10]=2[C:9](=O)[CH2:8]1.[C:20]([NH:23][NH2:24])([NH2:22])=[NH:21].Cl.Cl.O>C(O)C>[ClH:1].[Cl:1][C:2]1[S:3][C:4]([Cl:19])=[CH:5][C:6]=1[CH:7]1[CH2:16][C:15]2[N:14]=[CH:13][CH:12]=[C:11]([CH3:17])[C:10]=2[C:9](=[N:24][NH:23][C:20]([NH2:22])=[NH:21])[CH2:8]1
In ethanol (10 ml) was dissolved (−)-7-(2,5-dichlorothiophen-3-yl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (0.35 g), and to the mixture were added aminoguanidine hydrochloride (0.15 g), concentrated hydrochloric acid (0.28 ml) and water (0.28 ml). The mixture was refluxed for 4 hours, and under reduced pressure, the solvent was evaporated. The residue was dissolved in water, and the mixture was washed with ethyl acetate and concentrated under reduced pressure. The residue was heated in a little amount of ethanol, and the solution was cooled. Precipitated crystals were filtered off, and the mother liquor was concentrated to give crystals, which were recrystallized from water to give (−)-7-(2,5-dichlorothiophen-3-yl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline hydrochloride (Compound 109) (0.47 g) as colorless crystals.
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