2-Pyridone → N-(4-Fluorobenzyl)-4-methyl-2-(2-oxopyridin-1(2H)-yl)thiazole-5-carboxamide

HRID 1887292

Reaktionsgleichung

Reaktionsgleichung von HRID 1887292
[NH:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]1=[O:7].Br[C:9]1[S:10][C:11]([C:15]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)=[O:16])=[C:12]([CH3:14])[N:13]=1>>[F:25][C:22]1[CH:21]=[CH:20][C:19]([CH2:18][NH:17][C:15]([C:11]2[S:10][C:9]([N:1]3[CH:6]=[CH:5][CH:4]=[CH:3][C:2]3=[O:7])=[N:13][C:12]=2[CH3:14])=[O:16])=[CH:24][CH:23]=1

Komponenten

3

Edukt 2

HCID 88712-PyridoneHCID 666314052-Bromo-N-(4-fluorobenzyl)-4-methylthiazole-5-carboxamide

Produkt 1

HCID 24985443N-(4-Fluorobenzyl)-4-methyl-2-(2-oxopyridin-1(2H)-yl)thiazole-5-carboxamideAusbeute 45 %

Versuchsvorschrift

Following the procedure as described in Example 3, making variations only as required to use pyridin-2(1H)-one in place of 4-aminopyridin-2(1H)-one to react with 2-bromo-N-(4-fluorobenzyl)-4-methylthiazole-5-carboxamide in place of N-benzyl-2-bromo-4-methylthiazole-5-carboxamide, the title compound was obtained as a colorless solid in 45% yield: mp 170-172° C. (hexane/ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 8.80-8.77 (m, 1H), 7.47-7.42 (m, 1H), 7.34-7.28 (m, 2H), 7.03 (t, J=8.6 Hz, 2H), 6.75 (d, J=9.4 Hz, 1H), 6.44 (d, J=6.9 Hz, 1H), 6.06 (t, J=5.6 Hz, 1H), 4.56 (d, J=5.6 Hz, 2H), 2.70 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 163.9, 162.1, 160.6, 153.2, 152.5, 139.9, 133.5, 131.2, 129.6, 129.5, 122.9, 121.3, 115.8, 115.5, 107.8, 43.4, 17.3; (ES+) m/z 344.2 (M+1).

Quellen und Nachweise

ORD-Eintrag
ord-f0cfe239dbab43d5a961670bfbea5c62
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501746B2

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