Cl.[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([F:21])=[C:7]([CH:9]2[CH2:18][C:17]3[N:16]=[CH:15][CH:14]=[C:13]([CH3:19])[C:12]=3[C:11](=O)[CH2:10]2)[CH:8]=1.[C:22]([NH:25][NH2:26])([NH2:24])=[NH:23].Cl.Cl>C(O)C>[ClH:2].[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([F:21])=[C:7]([CH:9]2[CH2:18][C:17]3[N:16]=[CH:15][CH:14]=[C:13]([CH3:19])[C:12]=3[C:11](=[N:26][NH:25][C:22]([NH2:24])=[NH:23])[CH2:10]2)[CH:8]=1To a solution of 7-(5-chloro-2-fluorophenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one hydrochloride (0.6 g) and aminoguanidine hydrochloride (0.233 g) in ethanol (10 ml) was added concentrated hydrochloric acid (0.1 ml), and the mixture was stirred at 110° C. (bath temperature) for 2 hours. The reaction solution was cooled to room temperature, and the crystals were filtered and dried to give 7-(5-chloro-2-fluorophenyl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline hydrochloride (Compound 171) (0.6 g) as colorless crystals.
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