Aminopyrazine → 3-[7-Fluoro-2-(4-fluoro-benzyl)-3-oxo-2,3-dihydro-1H-isoindol-1-yl]-N-pyrazin-2-yl-propionamide
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]=C[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].[N:34]1C=CN=CC=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]=[N:34][CH:19]=[CH:18][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]Participants
3
Procedure
The product from Example 11, Part D (100 mg, 0.3 mmol) and pyrazin-2-ylamine (43 mg, 0.45 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 (8 mg, 7%). 1H NMR (300 MHz, CDCl3) δ 9.42 (s, 1H), 8.31 (d, J=3 Hz, 1H), 8.15 (m, 1H), 7.83 (s, 1H), 7.68 (d, J=8 Hz, 1H), 7.46 (m, 1H), 7.32 (m, 2H), 7.20 (t, J=9, 1H), 7.02 (t, J=7 Hz, 2H), 5.25 (d, J=15 Hz, 1H), 4.71 (m, 1H), 4.25 (d, J=15 Hz, 1H), 2.61 (m, 1H), 2.52 (m, 1H), 2.00 (m, 2H). MS: m/z (MH+) 409.
Sources & evidence
- ORD record
- ord-ca17eceb20904b709cfa59ebba6b2e43
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08796313B2
Reaction notes
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