1,4-Dioxane hydrochloride → methyl 5-{3-[4-(1-aminocyclobutyl)phenyl]-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-2-yl}pyridine-2-carboxylate tetrahydrochloride

Participants

Reaction Steps

Methyl 5-[3-(4-{1-[(tert-butoxycarbonyl)amino]cyclobutyl}phenyl)-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-2-yl]pyridine-2-carboxylate (52 mg, 0.085 mmol) in MeOH (0.5 mL) was added 4N HCl-dioxane (2 mL) and stirred at r.t for 23 hours. The mixture was concentrated to afford the desired product (49 mg, 88%) as an orange solid. 1HNMR (DMSO-d6) 400 MHz δ: 8.70-8.68 (m, 1H), 8.65 (br s, 1H), 8.63 (s, 1H), 8.56 (d, J=2.3 Hz, 1H), 8.16 (dd, J=8.0 Hz and 2.3 Hz, 1H), 8.10 (dd, J=4.6 Hz and 1.7 Hz, 1H), 8.04 (d, J=8.0 Hz, 1H), 7.97 (dd, J=8.0 Hz and 1.7 Hz, 1H), 7.57 (d, J=8.6 Hz, 2H), 7.39-7.35 (m, 3H), 7.29 (d, J=7.4 Hz, 1H), 7.12 (td, J=8.0 Hz and 1.1 Hz, 1H), 6.91 (dd, J=8.6 Hz and 1.1 Hz, 1H), 6.73 (dd, J=8.0 Hz and 4.6 Hz, 1H), 3.84 (s, 3H), 2.60-2.56 (m, 2H), 2.55-2.50 (m, 2H), 2.21-2.13 (m, 1H), 1.86-1.77 (m, 1H). LCMS: 515 [M+H].

Provenance & Evidence