2-Amino-5-fluoropyridine → 3-[7-Fluoro-2-(4-fluoro-benzyl)-3-oxo-2,3-dihydro-1H-isoindol-1-yl]-N-(5-fluoro-pyridin-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]=[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].NC1C=CC([F:41])=CN=1>>[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]([F:41])=[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]Participants
3
Procedure
The product from Example 11, Part D (100 mg, 0.3 mmol) and 2-amino-5-fluoropyridine (110 mg, 0.45 mmol) were converted to the title compound in a manner analogous to the method described in Example 7, Part E, using 2; 1 THF/CH2Cl2 in place of THF in the reaction and EtOAc in the workup, and without crystallization (120 mg, 93%). 1H NMR (400 MHz, CDCl3) δ 8.43 (s, 1H), 8.13 (m, 1H), 7.92 (d, J=3 Hz, 1H), 7.65 (d, J=8, 1H), 7.43 (m, 2H), 7.30 (m, 2H), 7.17 (t, J=9 Hz, 1H), 7.00 (t, J=9 Hz, 2H), 5.25 (d, J=15 Hz, 1H), 4.69 (m, 1H), 4.23 (d, J=15 Hz, 1H), 2.57 (m, 2H), 1.97 (m, 2H). MS: m/z (MH+) 426.
Sources & evidence
- ORD record
- ord-7bccef9000644d2cb4834cda4a121f5d
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08796313B2
Reaction notes
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