3,4-Difluorobenzylamine → N-(3,4-Difluorobenzyl)-2-(4-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamide

HRID 1887276

反応式

HRID 1887276 の反応式
[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:20]=[C:21]([CH2:26][NH2:27])[CH:22]=[CH:23][C:24]=1[F:25]>>[F:18][C:19]1[CH:20]=[C:21]([CH:22]=[CH:23][C:24]=1[F:25])[CH2:26][NH:27][C:14]([C:10]1[S:9][C:8]([N:5]2[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][C:4]2=[O:17])=[N:12][C:11]=1[CH3:13])=[O:16]

参加物

3

反応物 2

HCID 1235723,4-DifluorobenzylamineHCID 547423412-(4-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxylic acid

生成物 1

HCID 57744453N-(3,4-Difluorobenzyl)-2-(4-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamide収率 88%

実験手順

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 (3,4-difluorophenyl)methanamine, the title compound was obtained as a colorless solid in 88% yield: mp 294-296° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, DMSO-d6) δ 11.50 (br s, 1H), 8.77 (t, J=5.8 Hz, 1H), 8.59 (d, J=8.0 Hz, 1H), 7.40-7.28 (m, 2H), 7.15-7.10 (m, 1H), 6.26 (dd, J=8.0, 2.6 Hz, 1H), 5.82 (d, J=2.6 Hz, 1H), 4.35 (d, J=5.8 Hz, 2H), 2.53 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 167.9, 162.1, 161.6, 154.2, 150.5, 137.7, 132.6, 124.5, 123.3, 117.8, 117.6, 116.8, 116.6, 104.4, 98.0, 42.2, 17.5; MS (ES+) m/z 378.2 (M+1).

出典と根拠

ORDレコード
ord-fa47398696684a55997c9ca9e5c8fb20
出典データセット
uspto-grants-2013_08
特許番号
US08501746B2

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