1,4-Dioxane hydrochloride → 1-{4-[2-(1,3-Benzothiazol-2-yl)-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl]phenyl}cyclobutanamine trihydrochloride

Participants

Reaction Steps

tert-Butyl (1-{4-[2-(1,3-benzothiazol-2-yl)-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl]phenyl}cyclobutyl)carbamate (24.8 mg, 0.0405 mmol) was dissolved in DCM (1 mL). 4M HCl/dioxane (1 mL) was added to the mixture and stirred at room temperature for 18 hours. The mixture was concentrated and solidified with ether. The precipitated solids were collected by filtration and washed with ether to afford desired product (21.8 mg, 86.4%) as yellow solid. 1HNMR (DMSO-d6) 400 MHz δ: 8.85-8.65 (m, 3H), 8.16 (dd, J=4.8, 1.6 Hz, 1H), 8.11-8.07 (m, 1H), 7.97 (dd, J=7.8, 1.8 Hz, 1H), 7.83-7.78 (m, 1H), 7.65-7.55 (m, 4H), 7.51-7.46 (m, 1H), 7.45-7.39 (m, 2H), 7.37-7.32 (m, 1H), 7.21-7.15 (m, 1H), 6.98 (dd, J=8.0, 1.6 Hz, 1H), 6.79 (dd, J=8.0, 4.8 Hz, 1H), 2.66-2.54 (m, 4H), 2.28-2.15 (m, 1H), 1.92-1.77 (m, 1H); LCMS: 513 [M+H].

Provenance & Evidence