Chlorosuccinimide → tert-butyl {1-[4-(2-chloro-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl)phenyl]cyclobutyl}carbamate

Participants

Reaction Steps

A mixture of tert-butyl {1-[4-(9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl)phenyl]cyclobutyl}carbamate (5.00 g, 10 mmol) and N-chlorosuccinimide (1.39 g, 10 mmol) in chloroform (100 mL) was heated to refluxed temperature for 22 hours. After cooling to room temperature the solvent was evaporated in vacuo. The crude product was purified by silica gel chromatography (hexane/ethyl acetate; 0-100% ethyl acetate over 60 min) to give a yellow solid (75%). 1HNMR (CDCl3) 400 MHz δ: 8.06 (dd, J=5.0, 1.4 Hz, 1H), 8.03 (dd, J=7.8, 1.8 Hz, 1H), 7.40 (d, J=8.3 Hz, 2H), 7.32 (td, J=7.7, 1.5 Hz, 1H), 7.22 (d, J=8.3 Hz, 2H), 7.12 (td, J=7.6, 0.92 Hz, 1H), 6.94 (dd, J=8.3, 0.92 Hz, 1H) 6.88 (d, J=8.3 Hz, 1H), 6.66 (dd, J=7.8, 4.6 Hz, 1H), 6.30 (s, 1H), 5.10 (s, 1H), 2.59-2.38 (m, 4H), 2.19-2.07 (m, 1H), 1.95-1.83 (m, 1H), 1.48-1.21 (m, 9H); LC/MS [M+H]: 514.

Provenance & Evidence