4-Fluorobenzylamine → N-(4-Fluorobenzyl)-2-(4-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamide

HRID 1887264

Reaktionsgleichung

Reaktionsgleichung von HRID 1887264
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.[OH:10][C:11]1[CH:16]=[CH:15][N:14]([C:17]2[S:18][C:19]([C:23](O)=[O:24])=[C:20]([CH3:22])[N:21]=2)[C:13](=[O:26])[CH:12]=1>>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:7][C:23]([C:19]2[S:18][C:17]([N:14]3[CH:15]=[CH:16][C:11]([OH:10])=[CH:12][C:13]3=[O:26])=[N:21][C:20]=2[CH3:22])=[O:24])=[CH:4][CH:3]=1

Komponenten

3

Edukt 2

HCID 673264-FluorobenzylamineHCID 547423412-(4-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxylic acid

Produkt 1

HCID 54742339N-(4-Fluorobenzyl)-2-(4-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamideAusbeute 37 %

Versuchsvorschrift

Following the procedure as described in Example 1, making variations only as required to use 4-fluorobenzylamine in place of benzylamine to react with 2-(4-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxylic acid, the title compound was obtained as a colorless solid in 37% yield: mp 280-282° C. (methanol/ethyl acetate); 1H NMR (300 MHz, DMSO-d6) δ 8.74 (t, J=5.9 Hz, 1H), 8.56 (d, J=8.0 Hz, 1H), 7.34-7.29 (m, 2H), 7.12 (t, J=8.9 Hz, 2H), 6.22 (dd, J=8.0, 2.5 Hz, 1H), 5.75 (d, J=2.5 Hz, 1H), 4.35 (d, J=5.8 Hz, 2H), 2.52 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 167.9, 162.0, 161.6, 154.1, 150.2, 139.9, 132.6, 128.7, 127.7, 127.2, 123.6, 104.4, 98.0, 43.1, 17.5; MS (ES+) m/z 360.1 (M+1).

Quellen und Nachweise

ORD-Eintrag
ord-7cf9a9fc8c984605bf3f46dc6e81ab99
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501746B2

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