Reaktionsgleichung
[C:1]1([CH2:7][CH2:8][CH:9]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:11]([NH:18][C:19]([C:21]1[S:25][C:24]([N:26]2[CH2:31][CH2:30][CH2:29][CH2:28][C:27]2=[O:32])=[N:23][C:22]=1[CH3:33])=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[CH2:11]([NH:18][C:19]([C:21]1[S:25][C:24]([N:26]2[CH2:31][CH2:30][CH2:29][CH:28]([CH2:9][CH2:8][CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:27]2=[O:32])=[N:23][C:22]=1[CH3:33])=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1Komponenten
Versuchsvorschrift
Following the procedure as described in Example 3, making variations as required to use 3-phenylpropanal in place of cyclopropanecarbaldehyde to react with N-benzyl-4-methyl-2-(2-oxopiperidin-1-yl)thiazole-5-carboxamide in place of N-(4-fluorobenzyl)-4-methyl-2-(2-oxopyrrolidin-1-yl)thiazole-5-carboxamide, the title compound was obtained as a white solid in 10% yield: mp 140-141° C. (hexanes/ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 7.37-7.10 (m, 10H), 5.98 (t, J=4.7 Hz, 1H), 4.55 (d, J=5.3 Hz, 2H), 4.31-4.19 (m, 1H), 4.04-3.91 (m, 1H), 2.69-2.47 (m, 6H), 2.11-1.78 (m, 4H), 1.76-1.53 (m, 4H); 13C NMR (75 MHz, CDCl3) δ 172.8, 162.7, 157.0, 152.2, 142.0, 137.9, 128.8, 128.4, 128.3, 127.9, 127.6, 125.9, 119.2, 47.9, 44.1, 42.2, 35.9, 31.4, 28.9, 25.5, 21.3, 17.4; MS (ES+) m/z 448.21 (M+1).
Quellen und Nachweise
- ORD-Eintrag
- ord-e54a3ab3051d46b6ae74f8afc35ac400
- Quelldatensatz
- uspto-grants-2012_08
- Patentnummer
- US08236835B2
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