Ethyl 2-aminopyridine-4-carboxylate → 2-{3-[7-Fluoro-2-(4-fluoro-benzyl)-3-oxo-2,3-dihydro-1H-isoindol-1-yl]-propionylamino}-isonicotinic 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]([NH:15][C:16]1[CH:24]=[CH:23][C:19](C(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].[CH2:34]([O:36][C:37](=[O:45])C1C=CN=C(N)C=1)[CH3:35]>>[CH2:34]([O:36][C:37](=[O:45])[C:23]1[CH:19]=[CH:18][N:17]=[C:16]([NH:15][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:24]=1)[CH3:35]Participants
3
Reactant 2
Product 1
Procedure
The product from Example 11, Part D (100 mg, 0.30 mmol) and 2-aminoisonicotinic acid ethyl ester (75 mg, 0.45 mmol) were converted to the title compound in a manner analogous to the method described in Example 7, Part E without crystallization (120 mg, 83%). 1H NMR (300 MHz, CDCl3) δ 8.61 (s, 1H), 8.31 (d, J=5 Hz, 1H), 7.81 (s, 1H), 7.70 (d, J=8 Hz, 1H), 7.58 (dd, J=5 Hz, 1 Hz, 1H), 7.47 (m, 1H), 7.32 (m, 2H), 7.20 (t, J=9 Hz, 1H), 7.02 (t, J=9 Hz, 2H), 5.27 (d, J=15 Hz, 1H), 4.71 (m, 1H), 4.41 (q, J=7 Hz, 2H), 4.24 (d, J=15 Hz, 1H), 2.55 (m, 2H), 1.97 (m, 2H), 1.41 (t, J=7 Hz, 3H). MS: m/z (MH+) 480.
Sources & evidence
- ORD record
- ord-356eac09035048f6a6a8c0cf8df21ffb
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08796313B2
Reaction notes
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