Hydrochloric Acid → n-[2-[n-Ethyl-n-[2-(2-fluoropyridin-3-yloxy)ethyl]amino]ethyl]-6-iodoquinoxaline-2-carboxamide dihydrochloride salt

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Reaction Steps

To a solution of compound 10 (0.23 g, 0.45 mmol) in anhydrous dichloromethane (5 mL) was added, under argon, a 2.0 N hydrochloric acid solution in anhydrous ether (10 mL). The mixture was stirred at room temperature for 10 min and the solvent was evapored under vacuum. The residue was then suspended in anhydrous ether (10 mL) and the mixture was stirred, under argon, at room temperature for one night. The precipitate was collected by filtration to give compound 11 (0.24 g, 0.41 mmol) as a very hygroscopic beige solid. Yield 91%; mp 99-101° C. (dec.); IR (KBr) ν 1464, 1533, 1560, 1671, 2400-2700, 2800-3100, 3200-3400 cm−1; 1H NMR (200 MHz, DMSO-d6) δ 1.31 (t, 3H, J=7.0 Hz), 3.40 (m, 4H), 3.78 (m, 4H), 4.19 (m, 6H), 4.55 (t, 2H, J=3.5 Hz), 7.28 (dd, 1H, J=5.3, 7.7 Hz), 7.70 (m, 2H), 7.90 (d, 1H, J=8.8 Hz), 8.25 (dd, 1H, J=1.9, 8.8 Hz), 8.64 (d, 1H, J=1.8 Hz), 9.40 (m, 2H), 10.53 (se, 1H); ESI-MS m/z 509.9 [M+H]+; Anal. Calcd for C20H21O2IN5F, 2HCl, H2O: C, 40.02; H, 4.20; N, 11.67. Found: C, 40.40; H, 4.34; N, 11.28.

Provenance & Evidence