6-[(4-tert-butylphenyl)sulfonyl]-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine-8-carbonitrile → 6-[(4-tert-Butylphenyl)sulfonyl]-7-methyl-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine-8-carbonitrile

Participants

Reaction Steps

The title compound was prepared from 8-bromo-6-[(4-tert-butylphenyl)sulfonyl]-7-methyl-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine (intermediate 63) according to the procedure described for intermediate 54. Racemic mixture: LC/MS: m/e 501.0 (M+H)+. 1H NMR (500 MHz, CD3OD): δ 7.63 (1H, d), 7.47 (1H, d), 7.19 (2H, d), 7.13 (1H, d), 7.00 (2H, d), 5.20 (1H, d), 4.45 (1H, d), 2.65 (3H, s), 1.25 (9H, s). The racemic mixture was separated into individual enantiomers via chromatography on a Chiracel OD column eluting with 15% EtOH in hexanes at 8.0 mL/min. The faster eluting enantiomer E1 has a retention time of 9.77 min. The slower eluting enantiomer E2 has a retention time of 12.04 min.

Provenance & Evidence