Reaktionsgleichung
[CH3:1][O:2][CH2:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[CH3:19])[C:7]([OH:9])=O.[NH2:20][C:21](=[N:39][OH:40])[C:22]1[CH:37]=[CH:36][C:25]([C:26]([NH:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[O:27])=[C:24]([F:38])[CH:23]=1>>[F:38][C:24]1[CH:23]=[C:22]([C:21]2[N:20]=[C:7]([C:6]3[CH:10]=[CH:11][C:12]([N:13]4[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]4[CH3:19])=[C:4]([CH2:3][O:2][CH3:1])[CH:5]=3)[O:9][N:39]=2)[CH:37]=[CH:36][C:25]=1[C:26]([NH:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[O:27].[F:38][C:24]1[CH:23]=[C:22]([C:21]2[N:20]=[C:7]([C:6]3[CH:10]=[CH:11][C:12]([N:13]4[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]4[CH3:19])=[C:4]([CH2:3][O:2][CH3:1])[CH:5]=3)[O:40][N:39]=2)[CH:37]=[CH:36][C:25]=1[C:26]([NH:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32])=[O:27]Komponenten
4
Edukt 2
Produkt 2
Versuchsvorschrift
Ethyl N-(2-fluoro-4-{5-[3-(methoxymethyl)-4-(2-methylpiperidin-1-yl)phenyl]-1,2,4-oxadiazol-3-yl}benzoyl)-beta-alaninate was prepared following the general procedure 3 starting from Intermediate 2 and Intermediate 6. It was hydrolyzed following general procedure 9 to afford the title compound as a pale yellow powder. 1H NMR (DMSO-d6, 300 MHz) δ 12.3 (brs, 1H), 8.56 (m, 1H), 8.18 (m, 1H), 8.06 (m, 1H), 7.97 (m, 1H), 7.90 (dd, J=8.0 Hz, 1H), 7.81 (t, 1H, J=7.6 Hz), 7.38 (d, J=8.5 Hz, 1H), 4.54 (m, 2H), 3.47 (m, 2H), 3.40 (s, 3H), 3.23 (m, 1H), 3.02 (m, 1H), 2.56-2.47 (m, 3H), 1.88-1.30 (m, 7H), 0.85 (d, J=6.2 Hz, 3H). LC/MS (Method B): 497.4 (M+H)1, 495.4 (M−H)−. HPLC (Method A) Rt 3.01 min (Purity: 97.2%).
Quellen und Nachweise
- ORD-Eintrag
- ord-493a28c67e0e4f35b8d7d0e5fd19a8e9
- Quelldatensatz
- uspto-grants-2014_08
- Patentnummer
- US08815919B2
Verknüpfte Notizen
Wird geladen…