Acetyl chloride → HCID 11710146, compound

Participants

Reaction Steps

A solution of N1-(3-aminopropyl)-2-ethoxymethyl-1H-imidazo[4,5-c]quinoline-1,4-diamine (1.00 g, 3.18 mmol) in 15 mL of CH2Cl2 was placed under an atmosphere of nitrogen. The solution was chilled in an ice water bath and treated first with triethylamine (0.89 mL, 6.7 mmol) and then slowly with acetyl chloride (0.89 mL, 3.3 mmol). After 2 h, the reaction was warmed to ambient temperature, quenched with 15 mL of saturated NaHCO3 solution and diluted with 30 mL of CHCl3. The phases were separated and the organic portion was washed with H2O (15 mL) and brine (15 mL). The organic portion was dried over Na2SO4, filtered and concentrated under reduced pressure to yield a light yellow foam. The foam was crystallized from MeCN to give light yellow crystals. The crystals were pulverized and then triturated with Et2O for 18 h and filtered off to yield N-(3-{[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]amino}propyl)acetamide (0.728 g) as a white solid. mp 178–181° C.; 1H NMR (500 MHz, DMSO-d6) δ 8.44 (d, J=8.1 Hz, 1H), 7.82 (t, J=5.1 Hz, 1H), 7.59 (d, J=8.2 Hz, 1H), 7.45–7.42 (m, 1H), 7.26–7.22 (m, 1H), 6.96 (t, J=5.6 Hz, 1H), 6.59 (s, 2H), 4.75 (s, 2H), 3.61 (q, J=7.0 Hz, 2H), 3.20–3.14 (m, 4H), 1.77 (s, 3H), 1.71 (p, J=7.0 Hz, 2H), 1.17 (t, J=7.0Hz, 3H);

Provenance & Evidence