Reaction equation
I[CH3:2].[F:3][C:4]1[CH:5]=[C:6]([CH:25]=[CH:26][C:27]=1[F:28])[CH2:7][NH:8][C:9]([C:11]1[S:15][C:14]([N:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][C:17]2=[O:23])=[N:13][C:12]=1[CH3:24])=[O:10]>>[F:3][C:4]1[CH:5]=[C:6]([CH:25]=[CH:26][C:27]=1[F:28])[CH2:7][NH:8][C:9]([C:11]1[S:15][C:14]([N:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:2])=[CH:18][C:17]2=[O:23])=[N:13][C:12]=1[CH3:24])=[O:10]Participants
3
Procedure
Following the procedure as described in Example 9, making variation only as required to use iodomethane in place of 2-cyclopropylethyl 4-methylbenzenesulfonate to react with N-(3,4-difluorobenzyl)-2-(4-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamide, the title compound was obtained as a colorless solid in 66% yield: mp 183-185° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.65 (d, J=8.1 Hz, 1H), 7.18-7.05 (m, 3H), 6.20-6.15 (m, 2H), 5.97 (d, J=2.5 Hz, 1H), 4.53 (d, J=5.8 Hz, 2H), 3.82 (m, 3H), 2.68 (m, 3H); 13C NMR (75 MHz, CDCl3) δ 168.4, 162.3, 162.1, 153.6, 152.7, 135.0, 131.4, 123.7, 121.8, 117.6, 117.4, 116.9, 116.7, 104.0, 96.2, 56.0, 43.0, 17.3; MS (ES+) m/z 392.2 (M+1).
Sources & evidence
- ORD record
- ord-22a3f3e2d4494962ad90791b70a0b147
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08501746B2
Linked notes
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