[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[CH:9][C:8]=1[NH2:17].Cl.N1C=C[CH:22]=[CH:21][CH:20]=1>>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=[C:20]1[CH2:21][CH3:22]Using the general method of Example 1 Part D, N4-(4-chlorobutyl)quinoline-3,4-diamine (˜35.75 mmol) was cyclized using triethyl orthopropioniate (7.56 g, 42.9 mmol) in the presence of pyridine hydrochloride (0.41 g). The crude product was purified by chromatography (silica gel eluting with 95/5 dichloromethane/methanol) to provide 7.5 g of 1-(4chlorobutyl)-2-ethyl-1H-imidazo[4,5-c]quinoline as a white powder.
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