[O-][CH2:2][CH3:3].[Na+].[CH2:5]([C:9]([NH2:11])=[O:10])[C:6]([NH2:8])=[NH:7].Cl.BrCC([C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1)=O>C(O)C>[NH2:7][C:6]1[NH:8][C:2]([C:19]2[CH:18]=[CH:17][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=2)=[CH:3][C:5]=1[C:9]([NH2:11])=[O:10]Under ice-cooling, sodium ethoxide (2.7 g, 40 mmol) was added to a suspension of malonamamidine hydrochloride (5.5 g, 40 mmol) in dehydrated ethanol (130 mL), and then the mixture was stirred for 20 minutes. 2-Bromoacetylnaphthalene (5.0 g, 20 mmol) was added thereto, and the whole was stirred at room temperature overnight. The reaction mixture was concentrated in vacuo, and the obtained residue was purified by silica gel column chromatography to give the title reference compound (1.5 g) as a black solid (Yield 30%).
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