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

Participants

Reaction Steps

To a solution of tert-butyl 4-(2-phenyl-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepin-3-yl)benzylcarbamate (0.100 g) in dichloromethane (4 mL) was added 4.0 M HCl in dioxane (1 mL). The reaction was stirred at room temperature for 2 hours and then diluted with ether (20 mL). The product was removed by filtration under reduced pressure and dried to give (4-(2-phenyl-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepin-3-yl)phenyl)methanamine hydrochloride as a bright yellow solid (0.085 g, 83% based on tris HCl salt). 1H NMR (DMSO-d6) 400 MHz δ 8.67 (br. s, 1 H), 8.42 (br. s, 3H), 8.13-8.10 (m, 1H), 7.98-7.95 (m, 1H), 7.51-7.42 (m, 4H), 7.39-7.38 (m, 1H), 7.35-7.26 (m, 5H), 7.15 (t, J=7.4 Hz, 1H), 6.93-6.90 (m, 1H), 6.78-6.73 (m, 1H), 4.06 (dd, JA=11.3 Hz, JB=5.9 Hz, 2H); LCMS: 416 [M+H]; Calc. for C27H21N5.3.26 HCl.0.12 dioxane.0.16 diethylether: C, 60.66; H, 4.86; N, 12.58. Found C, 60.66; H, 4.99; N, 12.58.

Provenance & Evidence