HCID 21936597, compound → HCID 10108776, compound

Participants

Reaction Steps

Tert-butyl 2-[2-(4-amino-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)ethoxy]ethylcarbamate (9.35 g, 23.4 mmol) was suspended in 150 mL of 2M HCl in EtOH and the mixture was heated to reflux with stirring. After 2 h, the reaction was cooled to room temperature and the HCl salt of the product was collected by vacuum filtration and rinsed with ether. The free base was made by dissolving the HCl salt in water and treating with 10% NaOH solution until the mixture was pH 12. The aqueous suspension was extracted with CH2Cl2 (10×50 mL). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated to give 6.62 g of 1-[2-(2-aminoethoxy)ethyl]-2-ethyl-1H-imidazo[4,5-c]quinolin-4-amine as a light yellow solid. mp=144-146° C.; 1H NMR (300 MHz, DMSO-d6) δ8.07 (d, J=7.5 Hz, 1 H), 7.61 (dd, J=1.0, 8.3 Hz, 1 H), 7.43-7.38 (m, 1 H), 7.25-7.17 (m, 1 H), 6.45 (s, 2 H), 4.71 (t, J=5.2 Hz, 2 H), 3.84 (t, J=5.2 Hz, 2 H), 3.27 (t, J=5.7 Hz, 2 H), 2.97 (q, J=7.5 Hz, 2 H), 2.51 (t, J=5.8 Hz, 2 H), 1.37 (t, J=7.5 Hz, 3 H), 1.25 (bs, 2 H); 13C NMR (75 MHz, DMSO-d6) δ155.2, 152.1, 145.1, 132.8, 126.6, 126.6, 121.3, 120.5, 115.2, 73.8, 69.4, 45.4, 41.6, 20.4, 12.2; MS m/z 300 (M+H)+; Anal. Calcd for C16H21N5O: C, 64.19; H, 7.07; N, 23.39. Found: C, 63.98; H, 6.96; N, 23.27.

Provenance & Evidence