4-Benzyloxy-2(1H)-pyridone → 5-(4-(Benzyloxy)-2-oxopyridin-1(2H)-yl)-N-(3-fluorobenzyl)-3-methylthiophene-2-carboxamide
Reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][NH:12][C:11](=[O:15])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:17]1[S:21][C:20]([C:22]([NH:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=2)=[O:23])=[C:19]([CH3:33])[CH:18]=1>>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:17]2[S:21][C:20]([C:22]([NH:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=3)=[O:23])=[C:19]([CH3:33])[CH:18]=2)[C:11](=[O:15])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
Procedure
Following the procedure as described in Example 3, making variations only as required to use 4-(benzyloxy)pyridin-2(1H)-one in place of 4-aminopyridin-2(1H)-one to react with 5-bromo-N-(3-fluorobenzyl)-3-methylthiophene-2-carboxamide in place of N-benzyl-2-bromo-4-methylthiazole-5-carboxamide, the title compound was obtained as a colorless solid in 45% yield: mp 140-141° C.; 1H NMR (300 MHz, CDCl3) δ 7.56 (d, J=7.8 Hz, 1H), 7.43-7.27 (m, 6H), 7.11 (d, J=7.8 Hz, 1H), 7.04 (d, J=9.6 Hz, 1H), 7.00-6.92 (m, 1H), 6.84 (s, 1H), 6.29 (t, J=5.7 Hz, 1H), 6.14 (dd, J=7.8, 2.7 Hz, 1H), 6.05 (d, J=2.7 Hz, 1H), 5.02 (s, 2H), 4.58 (d, J=5.7 Hz, 2H), 2.54 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 166.8, 164.6, 163.0, 163.0 (d, JC-F=246.6 Hz), 162.2, 161.3, 140.7 (d, JC-F=7.0 Hz), 139.9, 139.7, 134.7, 134.4, 130.2 (d, JC-F=8.2 Hz), 128.8, 128.7, 127.8, 126.7, 123.2 (d, JC-F=2.9 Hz), 121.9, 114.6 (d, JC-F=15.2 Hz), 114.3 (d, JC-F=14.4 Hz), 103.4, 98.1, 70.6, 43.3, 15.9; MS (ES+) m/z 449.3 (M+1).
Sources & evidence
- ORD record
- ord-cff53c7e9a974f42a0e4350cc0e9251e
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08501746B2
Reaction notes
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