Hydrochloric Acid → HCID 68969163, compound

Participants

Reaction Steps

A solution of tert-butyl 4-{4-amino-2-(ethoxymethyl)-7-[3-(2-oxopyrrolidin-1-yl)propoxy]-1H-imidazo[4,5-c]quinolin-1-yl}butylcarbamate (prepared as described in Example 397, 2.90 g, 5.23 mmol) in 4 M ethanolic hydrogen chloride was heated at reflux for 2 hours. The solution was allowed to cool to room temperature and a precipitate formed that was isolated by filtration to afford 2.52 g of 1-(3-{[4-amino-1-(4-aminobutyl)-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-7-yl]oxy}propyl)pyrrolidin-2-one dihydrochloride as a white powder, mp>250° C. 1H NMR (300 MHz, DMSO-d6) δ 13.92 (s, 1H), 9.30-8.40 (br s, 2H), 8.15 (d, J=9.2 Hz, 1H), 8.13-8.00 (m, 3H), 7.30 (d, J=2.5 Hz, 1H), 7.20 (dd, J=9.1, 2.4 Hz, 1H), 4.83 (s, 2H), 4.65-4.60 (m, 2H), 4.10 (t, J=6.1 Hz, 2H), 3.60 (q, J=7.0 Hz, 2H), 3.41-3.37 (m, 4H), 2.87-2.76 (m, 2H), 2.22 (t, J=8.0 Hz, 2H), 2.04-1.85 (m, 6H), 1.81-1.70 (m, 2H), 1.19 (t, J=7.0 Hz, 3H);

Provenance & Evidence