Reaktionsgleichung
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][C:9]([OH:11])=O.C1N=CN(C(N2C=NC=C2)=O)C=1.CCN(C(C)C)C(C)C.Cl.[F:34][C:35]([F:55])([F:54])[C:36]1[CH:41]=[CH:40][C:39]([C@@H:42]([C:44]2[C:49]([C:50]([F:53])([F:52])[F:51])=[CH:48][CH:47]=[CH:46][N:45]=2)[NH2:43])=[CH:38][CH:37]=1>C(Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][C:9]([NH:43][C@@H:42]([C:39]1[CH:40]=[CH:41][C:36]([C:35]([F:55])([F:34])[F:54])=[CH:37][CH:38]=1)[C:44]1[C:49]([C:50]([F:51])([F:52])[F:53])=[CH:48][CH:47]=[CH:46][N:45]=1)=[O:11]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of 3-(pyridin-2-yl)propanoic acid (89 mg, 0.586 mmol, Oakwood) and DCM (4 mL) were added CDI (95 mg, 0.586 mmol) and DIPEA (0.20 mL, 1.148 mmol). After 0.5 hours, the reaction was treated with a solution of (S)-(4-(trifluoromethyl)phenyl)(3-(trifluoromethyl)pyridin-2-yl)methanamine hydrochloride (Intermediate 1) (125 mg, 0.390 mmol) in DCM (1.5 mL). The solution was stirred at rt. After 4 days, the resulting product was adsorbed onto a plug of silica gel and chromatographed through a Redi-Sep® pre-packed silica gel column (4 g), eluting with 0% to 60% EtOAc in hexane, to provide the title compound as a colorless oil. 1H NMR (CDCl3, 300 MHz) δ ppm 8.79 (d, J=3.8 Hz, 1H), 8.45 (d, J=4.8 Hz, 1H), 7.96 (d, J=7.9 Hz, 1H), 7.78 (d, J=7.9 Hz, 1H), 7.44-7.52 (m, 3H), 7.34-7.43 (m, 3H), 7.03-7.12 (m, 2H), 6.63 (d, J=8.0 Hz, 1H), 3.11 (td, J=6.7 & 2.5 Hz, 2H), 2.74 (td, J=7.2 & 2.5 Hz, 2H). MS (ESI pos. ion) m/z: 454.0 (M+H).
Aufarbeitung
- waitAfter 4 days
- customchromatographed through a Redi-Sep® pre-packed silica gel column (4 g)
- washeluting with 0% to 60% EtOAc in hexane
Quellen und Nachweise
- ORD-Eintrag
- ord-69d86137f59b4d1abca6f759140e411e
- Quelldatensatz
- uspto-grants-2014_04
- Patentnummer
- US08710043B2
Verknüpfte Notizen
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