反应详情

A solution of 2-ethoxymethyl-N1-isopropyl-1H-imidazo[4,5-c]quinoline-1,4-diamine (0.700 g, 2.34 mmol) in 25 mL of trifluroacetic acid was treated with platinum(IV) oxide (0.27 g, 1.2 mmol) and the mixture was shaken under an atmosphere of hydrogen (3.8×105 Pa). After 15 h, the reaction mixture was filtered through a pad of CELITE filter agent, rinsed with 9:1:0.5 CHCl3:MeOH:trifluoroacetic acid (TFA) and concentrated under reduced pressure to yield a creamy white solid. The solid was triturated with concentrated NH4OH solution for 2 h and then extracted with CHCl3 (3×). The organic portion was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to yield a white foam. The foam was triturated with diethyl ether, filtered and dried under reduced pressure to yield 2-ethoxymethyl-N1-isopropyl-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinoline-1,4-diamine (0.376 g) as a fine white solid. mp 144–146° C.; 1H NMR (300 MHz, CDCl3) δ 5.08 (d, J=2.7 Hz, 1H), 4.92 (s, 2H), 4.78 (s, 2H), 3.61 (q, J=7.0 Hz, 2H), 3.53–3.43 (m, 1H), 3.07–3.03 (m, 2H), 2.85–2.81 (m, 2H), 1.92–1.79 (m, 4H), 1.25 (t, J=7.0 Hz, 3H), 1.08 (d, J=6.3 Hz, 6H); 13C NMR (75 MHz, CDCl3) δ 149.4, 148.9, 148.1, 138.8, 122.9, 107.4, 66.6, 65.4, 53.0, 32.5, 23.7, 23.2, 22.8, 20.5, 15.1; MS (APCI) m/z 304 (M+H)+; Anal. Calcd for C16H25N5O: C, 63.34; H, 8.31; N, 23.08; Found: C, 63.32; H, 8.31; N, 22.97.

1. filtrationthe reaction mixture was filtered through a pad of CELITE
2. filtrationfilter agent
3. washrinsed with 9:1:0.5 CHCl3
4. concentrationMeOH:trifluoroacetic acid (TFA) and concentrated under reduced pressure
5. customto yield a creamy white solid
6. customThe solid was triturated with concentrated NH4OH solution for 2 h
7. extractionextracted with CHCl3 (3×)
8. washThe organic portion was washed with brine
9. dry with materialdried over Na2SO4
10. filtrationfiltered
11. concentrationconcentrated under reduced pressure
12. customto yield a white foam
13. customThe foam was triturated with diethyl ether
14. filtrationfiltered
15. customdried under reduced pressure