HCID 59618815, compound → HCID 59618712, compound

Participants

Reaction Steps

To a solution of 1-[6-[(4-tert-butylphenyl)sulfonyl]-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepin-8-yl]ethanone (Example 454, 100 mg, 0.200 mmol) in THF (0.50 mL) was added borane-THF complex (0.700 mL of 1M solution). After stirring at rt for 2 h, the reaction mixture was cooled to 0° C. and was quenched with 3N HCl, and the stirring continued at rt for 1 h. The product was extracted into EtOAc, and the combined extracts were washed with water, brine, dried over MgSO4 and concentrated. The residue was purified by SiO2 column chromatography, eluting with mixtures of EtOAc in hexane, to provide title compound as a racemic mixture. LC/MS: m/e 506.0 (M+H)+. 1H NMR (500 MHz, CDCl3): δ 7.59 (1H, d, J=1.9 Hz), 7.56 (1H, d, J=7.3 Hz), 7.35 (1H, dd, J=8.4, 2.0 Hz), 7.12 (21-1, d, J=8.4 Hz), 7.05 (1H, d, J=7.5 Hz), 6.96 (2H, d, J=8.5 Hz), 6.85 (1H, s), 6.74 (1H, d, J=8.3 Hz), 4.95 (1H, q, J=6.4 Hz), 4.80 (1H, br s), 1.57 (3H, d, J=6.7 Hz), 1.26 (9H, s). The racemic mixture was separated into its enantiomers eluting on a Chiracel AD-H column (isocratic 15% EtOH in hexanes, 8 mL/min, 254 nM) with retention time of 22 min and 33 min, respectively. Faster enantiomer E1: LC/MS: m/e 506.0 (M+H)+. Slower enantiomer E2: LC/MS: m/e 506.0 (M+H).

Provenance & Evidence