2-Oxo-N-phenyl-1,2-dihydropyridine-3-carboxamide → N-Benzyl-4-methyl-2-(2-oxo-3-(phenylcarbamoyl)pyridin-1(2H)-yl)thiazole-5-carboxamide

HRID 1887295Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1887295
[O:1]=[C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:9])=[CH:6][CH:5]=[CH:4][NH:3]1.[CH2:17]([NH:24][C:25]([C:27]1[S:31][C:30](Br)=[N:29][C:28]=1[CH3:33])=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[CH2:17]([NH:24][C:25]([C:27]1[S:31][C:30]([N:3]2[CH:4]=[CH:5][CH:6]=[C:7]([C:8](=[O:9])[NH:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:2]2=[O:1])=[N:29][C:28]=1[CH3:33])=[O:26])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Komponenten

3

Edukt 2

HCID 128259952-Oxo-N-phenyl-1,2-dihydropyridine-3-carboxamideHCID 579593962-Bromo-4-methyl-thiazole-5-carboxylic acid benzylamide

Produkt 1

HCID 24985275N-Benzyl-4-methyl-2-(2-oxo-3-(phenylcarbamoyl)pyridin-1(2H)-yl)thiazole-5-carboxamideAusbeute 15 %

Versuchsvorschrift

Following the procedure as described in Example 3, making variations only as required to use 2-oxo-N-phenyl-1,2-dihydropyridine-3-carboxamide in place of 4-aminopyridin-2(1H)-one to react with N-benzyl-2-bromo-4-methylthiazole-5-carboxamide, the title compound was obtained as a colorless solid in 15% yield: mp 225-227° C. (hexane/ethyl acetate); 1H NMR (300 MHz, DMSO-d6) δ 13.14 (s, 1H), 8.64-8.55 (m, 2H), 8.18 (dd, J=6.6, 2.1 Hz, 1H), 7.58-7.47 (m, 5H), 7.32-7.26 (m, 4H), 7.24-7.17 (m, 1H), 6.75-6.70 (m, 1H), 4.37 (d, J=5.9 Hz, 2H), 2.44 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 162.0, 161.8, 156.0, 151.4, 146.0, 145.7, 140.2, 140.0, 129.7, 129.5, 128.7, 127.6, 127.2, 127.2, 120.1, 118.4, 107.8, 43.1, 17.4; (ES+) m/z 445.1 (M+1).

Quellen und Nachweise

ORD-Eintrag
ord-a5ed14510b4743709b5238b75fea4c84
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501746B2

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