Reaktionsgleichung
Br[C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10]3[N:12]=[C:13]([C:16]([F:19])([F:18])[F:17])[CH:14]=[CH:15][C:9]=3[CH2:8][N:7]([S:20]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[C:6]=2[C:33]=1[CH3:34].C(C1C=CC(S([N:48]2C3C=C(C#N)C=CC=3NC3N=C(C(F)(F)F)C=CC=3[CH2:49]2)(=O)=O)=CC=1)(C)(C)C>>[C:29]([C:26]1[CH:25]=[CH:24][C:23]([S:20]([N:7]2[C:6]3[C:33]([CH3:34])=[C:2]([C:49]#[N:48])[CH:3]=[CH:4][C:5]=3[NH:11][C:10]3[N:12]=[C:13]([C:16]([F:17])([F:18])[F:19])[CH:14]=[CH:15][C:9]=3[CH2:8]2)(=[O:21])=[O:22])=[CH:28][CH:27]=1)([CH3:31])([CH3:32])[CH3:30]Komponenten
3
Versuchsvorschrift
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.
Aufarbeitung
- customThe racemic mixture was separated into individual enantiomers via chromatography on a Chiracel OD column
- washeluting with 15% EtOH in hexanes at 8.0 mL/min
- washThe faster eluting enantiomer E1
- washThe slower eluting enantiomer E2
Quellen und Nachweise
- ORD-Eintrag
- ord-73f9fbd8cbbd48d0b741f9c509869484
- Quelldatensatz
- uspto-grants-2012_04
- Patentnummer
- US08153626B2
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