HCID 10108777, compound → HCID 10017869, compound

Participants

Reaction Steps

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.

Provenance & Evidence