8-Hydroxyquinoline → 2-(4-Amino-2-oxopyridin-1(2H)-yl)-N-benzyl-4-methylthiazole-5-carboxamide

HRID 1887282

反応式

HRID 1887282 の反応式
[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14](Br)=[N:13][C:12]=1[CH3:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:18][C:19]1[CH:24]=[CH:23][NH:22][C:21](=[O:25])[CH:20]=1.C(=O)([O-])[O-].[K+].[K+].OC1C=CC=C2C=1N=CC=C2>CS(C)=O.[Cu]I.O>[NH2:18][C:19]1[CH:24]=[CH:23][N:22]([C:14]2[S:15][C:11]([C:9]([NH:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:10])=[C:12]([CH3:17])[N:13]=2)[C:21](=[O:25])[CH:20]=1

参加物

8

反応物 4

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 5735304-Amino-1,2-dihydropyridin-2-oneHCID 579593962-Bromo-4-methyl-thiazole-5-carboxylic acid benzylamide

生成物 1

HCID 249852702-(4-Amino-2-oxopyridin-1(2H)-yl)-N-benzyl-4-methylthiazole-5-carboxamide収率 49.4%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

実験手順

To a degassed solution of N-benzyl-2-bromo-4-methylthiazole-5-carboxamide (1.58 g, 5.00 mmol), 4-aminopyridin-2(1H)-one (0.72 g, 6.50 mmol), potassium carbonate (2.00 g, 14.40 mmol) and 8-hydroxyquinoline (0.08 g, 0.50 mmol) in dimethyl sulfoxide (30 mL) was added copper(I) iodide (0.10 g, 0.50 mmol). The reaction mixture was heated at 75-80 C. for 16 hours, then cooled to ambient temperature. Water (300 mL) was added to the mixture and the crude product was precipitated and collected by filtration. The crude product was subjected to column chromatography to afford the title compound as a white solid (0.84 g, 49%): mp 171-172° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.68 (t, J=5.7 Hz, 1H), 8.40 (d, J=7.8 Hz, 1H), 7.32-7.19 (m, 5H), 6.80 (s, 2H), 6.07 (dd, J=7.8, 1.8, Hz, 1H), 5.38 (d, J=1.8 Hz, 1H), 4.37 (d, J=5.7 Hz, 2H), 2.50 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 162.2, 160.8, 157.7, 154.6, 150.0, 140.0, 131.5, 128.7, 127.7, 127.1, 122.9, 103.4, 90.5, 43.0, 17.5; MS (ES+) m/z 341.2 (M+1).

後処理

  1. temperatureThe reaction mixture was heated at 75-80 C
  2. customthe crude product was precipitated
  3. filtrationcollected by filtration

出典と根拠

ORDレコード
ord-af9b9e96cf5346359289a645c60eeb0d
出典データセット
uspto-grants-2013_08
特許番号
US08501746B2

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