6-{3-[7-Fluoro-2-(4-fluorobenzyl)-3-oxo-2,3-dihydro-1H-isoindol-1-yl]-propionylamino}-nicotinic acid → 3-(6-{3-[7-Fluoro-2-(4-fluoro-benzyl)-3-oxo-2,3-dihydro-1H-isoindol-1-yl]-propionylamino}-pyridin-3-yl)-acrylic acid ethyl ester
Reaction equation
[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](NC1C=CC(C(O)=O)=CN=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].[CH2:34]([O:36][C:37](=[O:47])[CH:38]=[CH:39][C:40]1[CH:41]=[N:42][C:43]([NH2:46])=[CH:44][CH:45]=1)[CH3:35]>>[CH2:34]([O:36][C:37](=[O:47])[CH:38]=[CH:39][C:40]1[CH:41]=[N:42][C:43]([NH:46][C:13](=[O:14])[CH2:12][CH2:11][CH:9]2[C:10]3[C:6](=[CH:5][CH:4]=[CH:3][C:2]=3[F:1])[C:7](=[O:33])[N:8]2[CH2:25][C:26]2[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=2)=[CH:44][CH:45]=1)[CH3:35]Participants
3
Reactant 2
Product 1
Procedure
The product of Example 11, Part D (137 mg, 0.41 mmol) and 3-(6-amino-pyridin-3-yl)-acrylic acid ethyl ester (80 mg, 0.41 mmol) were converted to the title compound in a manner analogous to the method described in Example 27 (90.8 mg, 43%). 1H NMR (400 MHz, CDCl3) δ 8.3 (s, 1H), 8.18 (d, J=8.7 Hz, 1H), 8.03 (s, 1H); 7.89-7.86 (d, J=8.6 Hz, 1H); 7.71 (d, J=7 Hz, 1H); 7.62 (d, J=16 Hz, 1H), 7.49-7.44 (m, 1H); 7.34 (m, 2H); 7.23 (t, J=8.75 Hz, 1H); 7.04 (t, J=8.8 Hz, 2H); 6.44 (d, J=16 Hz, 1H); 5.28 (d, J=15 Hz, 1H), 4.70 (m, 1H), 4.29-4.23 (m, 3H); 2.57-2.50 (m, 2H); 2.04-1.93 (m, 2H); 1.36 (t, J=7.4 Hz, 3H) MS: m/z (MH+) 506.
Sources & evidence
- ORD record
- ord-14e413b8b3dd4e40adf8507519cf69b8
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08796313B2
Reaction notes
Loading…