Reaktionsgleichung
[F:1][CH:2]([F:12])[O:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Br)=[CH:6][CH:5]=1.[F:13][C:14]1[CH:37]=[CH:36][C:17]([CH2:18][NH:19][C:20]([C:22]2[S:26][C:25]([N:27]3[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][C:28]3=[O:34])=[N:24][C:23]=2[CH3:35])=[O:21])=[CH:16][CH:15]=1>>[F:1][CH:2]([F:12])[O:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][O:33][C:30]2[CH:31]=[CH:32][N:27]([C:25]3[S:26][C:22]([C:20]([NH:19][CH2:18][C:17]4[CH:16]=[CH:15][C:14]([F:13])=[CH:37][CH:36]=4)=[O:21])=[C:23]([CH3:35])[N:24]=3)[C:28](=[O:34])[CH:29]=2)=[CH:6][CH:5]=1Komponenten
Versuchsvorschrift
Following the procedure as described in Example 9, making variation only as required to use 4-(difluoromethoxy)benzyl bromide in place of 2-cyclopropylethyl 4-methylbenzenesulfonate to react with N-(4-fluorobenzyl)-2-(4-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamide, the title compound was obtained as a colorless solid in 25% yield: mp 242-244° C. (dichloromethane/methanol); 1H NMR (300 MHz, DMSO-d6) δ 8.78 (t, J=5.8 Hz, 1H), 8.60 (dd, J=8.1, 3.0 Hz, 1H), 7.56-7.47 (m, 2H), 7.34-7.08 (m, 7H), 6.43-6.32 (m, 1H), 6.22 (s, 1H), 5.15 (s, 2H), 4.34 (d, J=5.8 Hz, 2H), 2.52 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 167.4, 163.2, 161.9, 160.0, 151.4, 150.4, 136.1, 133.7, 132.7, 130.5, 129.8, 123.6, 120.1, 119.2, 116.7, 115.6, 113.3, 104.3, 97.5, 70.1, 44.6, 17.5; MS (ES+) m/z 516.4 (M+1).
Quellen und Nachweise
- ORD-Eintrag
- ord-982cc466994d459eba1b3d479d6fa97a
- Quelldatensatz
- uspto-grants-2013_08
- Patentnummer
- US08501746B2
Verknüpfte Notizen
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