[Cl:1][C:2]1[S:3][C:4]([Cl:22])=[CH:5][C:6]=1[CH:7]1[CH2:16][C:15]2[N:14]=[N:13][CH:12]=[C:11]([C:17]([F:20])([F:19])[F:18])[C:10]=2[C:9](=O)[CH2:8]1.[C:23]([NH:26][NH2:27])([NH2:25])=[NH:24].Cl.CS(O)(=O)=O.C1C=CC=CC=1>C(O)C>[Cl:1][C:2]1[S:3][C:4]([Cl:22])=[CH:5][C:6]=1[CH:7]1[CH2:16][C:15]2[N:14]=[N:13][CH:12]=[C:11]([C:17]([F:20])([F:19])[F:18])[C:10]=2[C:9](=[N:27][NH:26][C:23]([NH2:25])=[NH:24])[CH2:8]1
To a solution of 7-(2,5-dichlorothiophen-3-yl)-4-trifluoromethyl-5,6,7,8-tetrahydrocinnolin-5-one (0.443 g) and aminoguanidine hydrochloride (167 mg) in ethanol (10 ml) were added methanesulfonic acid (0.2 ml) and benzene (10 ml), and the mixture was refluxed for 1.5 hours. Under reduced pressure, the solvent was evaporated, and to the residue was added sodium hydrogen carbonate solution to make the solution alkaline. The mixture was extracted with ethyl acetate, and the organic layer was washed with water and concentrated under reduced pressure. The residue was washed with isopropylether and diethylether and dried to give 7-(2,5-dichlorothiophen-3-yl)-5-guanidinoimino-4-trifluoromethyl-5,6,7,8-tetrahydrocinnoline (Compound 135) (0.160 g) as colorless crystals.
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