Hydrochloric Acid → 1-(4-(2-phenyl-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepin-3-yl)phenyl)cyclobutanamine hydrochloride

Participants

Reaction Steps

To a solution of tert-butyl (1-(4-(2-phenyl-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepin-3-yl)phenyl)cyclobutyl)carbamate (0.55 g) in dichloromethane (50 mL) was added 4.0 M HCl in dioxane (5 mL). The reaction was stirred at room temperature for 6 hours and then diluted with ether (50 mL). The product was removed by filtration under reduced pressure and dried to give 1-(4-(2-phenyl-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepin-3-yl)phenyl)cyclobutanamine hydrochloride as a pale yellow solid (0.52 g, 88% based on tris HCl salt). 1H NMR (DMSO-d6) 400 MHz δ 8.80 (bs, 3H), 8.68 (s, 1H), 8.12 (dd, JA=4.8 Hz, JB=1.6 Hz, 1H), 7.98-7.95 (m, 1H), 7.57-7.48 (m, 4H), 7.43-7.27 (m, 7H), 7.15 (t, J=7.2 Hz, 1H), 6.91-6.88 (m, 1H), 6.79-6.74 (m, 1H), 2.56 (t, J=8 Hz, 4H), 2.24-2.16 (m, 1H), 1.85-1.77 (m, 1H); LCMS: 456 [M+H]. Calc. for C30H25N5.3.07HCl.0.14 dioxane.0.28 diethylether: C, 63.36; H, 5.37; N, 11.66. Found C, 63.36; H, 5.50; N, 11.67.

Provenance & Evidence