[CH:1]([NH:4][N:5]1[C:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N+:10]([O-])=[CH:9][C:8]=2[N:7]=[C:6]1[CH3:19])([CH3:3])[CH3:2].[NH4+:20].[OH-].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.C(Cl)(Cl)Cl>C(Cl)Cl.O>[CH:1]([NH:4][N:5]1[C:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:20])[C:8]=2[N:7]=[C:6]1[CH3:19])([CH3:3])[CH3:2]A solution of N-isopropyl(2-methyl-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl)amine (1.95 g, 7.61 mmol) in 75 mL of CH2Cl2 was treated with 35 mL of concentrated NH4OH solution. To the rapidly stirred solution was added p-toluenesulfonyl chloride (1.52 g, 7.99 mmol). After stirring for 30 min, the reaction mixture was treated with CHCl3 (25 mL) and H2O (35 mL). The layers were separated and the organic portion was washed with 2% Na2CO3 solution (2×), H2O and brine. The organic portion was dried over Na2SO4, filtered and concentrated to give a light-yellow solid. Crystallization from propyl acetate gave N1-isopropyl-2-methyl-1H-imidazo[4,5-c]quinoline-1,4-diamine (747 mg) as off-white crystals. mp 227–229° C.; 1H NMR (300 MHz, CDCl3) δ 8.19 (dd, J=8.2, 1.1 Hz, 1H), 7.79 (dd, J=8.4, 0.7 Hz, 1H), 7.53–7.45 (m, 1H), 7.33–7.26 (m, 1H), 5.42 (s, 2H), 4.91 (d, J=1.4 Hz, 1H), 3.73–3.62 (m, 1H), 2.64 (s, 3H), 1.15 (d, J=6.2 Hz, 6H); 13C NMR (75 MHz, CDCl3) δ 151.4, 151.3, 144.9, 133.3, 127.6, 127.3, 124.6, 122.4, 120.2, 115.4, 52.3, 20.9, 13.8; MS m/z 256 (M+H)+; Anal. Calcd for C14H17N5: C, 65.86; H, 6.71; N, 27.43; Found: C, 65.59; H, 6.56; N, 27.09.
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