反应详情

2-Ethyl-N1-isopropyl-1H-imidazo[4,5-c]quinoline-1,4-diamine was prepared in 5 steps from N′-(3-aminoquinolin-4-yl)hydrazine tert-butyl carboxylate in analogous fashion to the preparation of N1-Isopropyl-2-propyl-1H-imidazo[4,5-c]quinoline-1,4-diamine (Example 16). Triethyl orthopropionate was used in lieu of trimethyl orthobutyrate. The material was purified by chromatography (SiO2, 20% (80:18:2 CHCl3:MeOH:NH4OH) in CHCl3) to yield an off white solid. The solid was crystallized from MeCN to yield 2-ethyl-N1-isopropyl-1H-imidazo[4,5-c]quinoline-1,4-diamine (0.358 g) as light pink crystals. mp 245–247° C.; 1H NMR (500 MHz, DMSO-d6) δ 8.47 (d, J=8.1 Hz, 1H), 7.57 (d, J=8.0 Hz, 1H), 7.39 (t, J=7.5 Hz, 1H), 7.22 (t, J=7.5 Hz, 1H), 6.95 (s, 1H), 6.44 (s, 2H), 3.54–3.46 (m, 1H), 3.04–2.88 (m, 2H), 1.37 (t, J=7.1 Hz, 3H), 1.01 (d, J=5.8 Hz, 6H); 13C NMR (125 MHz, DMSO-d6) δ 155.6, 152.0, 145.0, 132.8, 126.8, 126.1, 124.1, 121.3, 120.9, 115.0, 51.2, 20.6, 19.7, 12.4; MS (APCI) m/z 270 (M+H)+; Anal. Calcd for C15H19N5: C, 66.89; H, 7.11; N, 26.00; Found: C, 66.81; H, 7.22; N, 25.95.

1. customThe material was purified by chromatography (SiO2, 20% (80:18:2 CHCl3:MeOH:NH4OH) in CHCl3)
2. customto yield an off white solid
3. customThe solid was crystallized from MeCN