2-Aminoquinoline → 3-[7-Fluoro-2-(4-fluoro-benzyl)-3-oxo-2,3-dihydro-1H-isoindol-1-yl]-N-quinolin-2-yl-propionamide
Reaktionsgleichung
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[CH:9]([CH2:11][CH2:12][C:13]([NH:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](O)=O)=[CH:18][N:17]=1)=[O:14])[N:8]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=1)[C:7]2=[O:33].N1C2C(=CC=CC=2)[CH:37]=[CH:36][C:35]=1N>>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[CH:9]([CH2:11][CH2:12][C:13]([NH:15][C:16]1[CH:24]=[CH:23][C:19]3[C:18](=[CH:35][CH:36]=[CH:37][CH:20]=3)[N:17]=1)=[O:14])[N:8]([CH2:25][C:26]1[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=1)[C:7]2=[O:33]Komponenten
3
Versuchsvorschrift
The product from Example 11, Part D (200 mg, 0.6 mmol) and quinolin-2-ylamine (131 mg, 0.91 mmol) were converted to the title compound in a manner analogous to the method described in Example 7, Part E, using CH2Cl2 in place of THF in the reaction and EtOAc in the workup, and without crystallization (220 mg, 80%). 1HNMR (400 MHz, CDCl3) δ 8.87 (s, 1H), 8.46 (s, 1H), 8.09 (s, 1H), 7.87 (d, J=8 Hz, 1H), 7.80 (d, J=8 Hz, 1H), 7.66 (m, 2H), 7.48 (t, J=7 Hz, 1H), 7.41 (m, 1H), 7.32 (m, 2H), 7.16 (t, J=9 Hz, 1H), 7.01 (t, J=7 Hz, 2H), 5.30 (d, J=15 Hz, 1H), 4.71 (m, 1H), 4.25 (d, J=15 Hz, 1H), 2.59 (m, 2H), 1.98 (m, 2H). MS: m/z (MH+) 458.
Quellen und Nachweise
- ORD-Eintrag
- ord-e15482c1bb254c5fa83e281564f77f88
- Quelldatensatz
- uspto-grants-2014_08
- Patentnummer
- US08796313B2
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