p-Fluorophenethylamine → N-(4-Fluorophenethyl)-2-(4-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamide

HRID 1887275Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1887275
[OH:1][C:2]1[CH:7]=[CH:6][N:5]([C:8]2[S:9][C:10]([C:14]([OH:16])=O)=[C:11]([CH3:13])[N:12]=2)[C:4](=[O:17])[CH:3]=1.[F:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][NH2:27])=[CH:21][CH:20]=1>>[F:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][NH:27][C:14]([C:10]2[S:9][C:8]([N:5]3[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][C:4]3=[O:17])=[N:12][C:11]=2[CH3:13])=[O:16])=[CH:21][CH:20]=1

Komponenten

3

Edukt 2

HCID 4653p-FluorophenethylamineHCID 547423412-(4-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxylic acid

Produkt 1

HCID 54742336N-(4-Fluorophenethyl)-2-(4-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamideAusbeute 69 %

Versuchsvorschrift

Following the procedure as described in Example 1, making variations only as required to use 2-(4-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxylic acid in place of 4-methyl-2-(2-oxo-4-phenylpyridin-1(2H)-yl)thiazole-5-carboxylic acid to react with 2-(4-fluorophenyl)ethanamine, the title compound was obtained as a colorless solid in 69% yield: mp 225-227° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, DMSO-d6) δ 11.47 (s, 1H), 8.57 (d, J=8.0 Hz, 1H), 8.23 (t, J=5.5 Hz, 1H), 7.25-7.18 (m, 2H), 7.12-7.04 (m, 2H), 6.25 (dd, J=8.0, 2.6 Hz, 1H), 5.81 (d, J=2.5 Hz, 1H), 3.42-3.35 (m, 2H), 2.78 (t, J=7.2 Hz, 2H), 2.50 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 167.8, 161.9, 161.6, 159.6, 154.1, 149.6, 136.0, 132.6, 130.9, 124.0, 115.5, 104.3, 98.0, 41.2, 34.5, 17.3; MS (ES+) m/z 374.2 (M+1).

Quellen und Nachweise

ORD-Eintrag
ord-c8adfbf9c95048eb86e8e0298567a62e
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501746B2

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