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

Participants

Reaction Steps

To a solution (S)-tert-butyl (1-(4-(2-phenyl-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepin-3-yl)phenyl)ethyl)carbamate (0.251 g) in dichloromethane (20 mL) was added 4.0 M HCl in dioxane (2 mL). The reaction was stirred at room temperature for 4 hours. The reaction mixture was concentrated under reduced pressure and then diluted with ether (20 mL). The product was removed by filtration under reduced pressure and dried to give (S)-1-(4-(2-phenyl-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepin-3-yl)phenyl)ethanamine hydrochloride as a yellow solid (0.215 g, 98% based on tris HCl salt). 1H NMR (DMSO-d6) 400 MHz δ 8.83 (br. s, 1 H), 8.69 (br. s, 3H), 8.16 (dd, JA=4.7 Hz, JB=1.6 Hz, 1H), 8.00 (d, J=7.8 Hz, 1H), 7.56 (d, J=8.6 Hz, 2H), 7.52-7.44 (m, 3H), 7.40-7.30 (m, 3H), 7.28 (d, J=8.2 Hz, 2H), 7.19 (t, J=7.6 Hz, 1H), 6.95-6.91 (m, 1H), 6.82-6.77 (m, 1H), 4.43 (quint., J=6.1 Hz, 1H), 1.52 (d, J=6.7 Hz, 3H); LCMS: 430 [M+H]; Calc. for C28H23N5.3.5HCl.0.05 dioxane.0.35 diethylether: C, 60.52; H, 5.22; N, 11.92. Found C, 60.57; H, 5.67; N, 12.02.

Provenance & Evidence