8-Hydroxyquinoline → N-Benzyl-4-methyl-2-(2-oxo-1-phenyl-1,2-dihydropyridine-4-carboxamido)thiazole-5-carboxamide

HRID 45385

反応式

HRID 45385 の反応式
[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([NH:16][C:17]([C:19]2[CH:24]=[CH:23][NH:22][C:21](=[O:25])[CH:20]=2)=[O:18])=[N:13][C:12]=1[CH3:26])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].O[C:34]1[CH:35]=[CH:36][CH:37]=[C:38]2[C:43]=1N=CC=C2.IC1C=CC=CC=1>CS(C)=O.[Cu]I>[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([NH:16][C:17]([C:19]2[CH:24]=[CH:23][N:22]([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:43]=3)[C:21](=[O:25])[CH:20]=2)=[O:18])=[N:13][C:12]=1[CH3:26])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 59369671N-Benzyl-4-methyl-2-(2-oxo-1,2-dihydropyridine-4-carboxamido)thiazole-5-carboxamide

生成物 1

HCID 59369687N-Benzyl-4-methyl-2-(2-oxo-1-phenyl-1,2-dihydropyridine-4-carboxamido)thiazole-5-carboxamide収率 20%

試薬・触媒・溶媒 2

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

反応条件

温度
130 °C

実験手順

To a degassed solution of N-benzyl-4-methyl-2-(2-oxo-1,2-dihydropyridine-4-carboxamido)thiazole-5-carboxamide (0.060 g, 0.16 mmol), potassium carbonate (0.033 g, 0.24 mmol) and 8-hydroxyquinoline (0.0034 g, 0.024 mmol) in dimethyl sulfoxide (5 mL) were added iodobenzene (0.039 g, 0.19 mmol) and finally copper(I) iodide (0.0046 g, 0.025 mmol). The reaction mixture was heated at 130° C. for 16 hours, then cooled to ambient temperature and filtered. The solvent was removed in vacuo. The residue was dissolved in dichloromethane (40 mL) and washed with saturated aqueous sodium bicarbonate solution (2×20 mL), and brine (20 mL). The organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrate in vacuo. The residue was recrystallized from ethyl acetate and methanol to yield a colorless solid in 20% yield (0.012 g); m.p. 260-262° C.; 1H NMR (DMSO-d6, 300 MHz) δ 13.11 (s, br., 1H), 8.63 (t, J=5.8 Hz, 1H), 7.78 (d, J=7.1 Hz, 1H), 7.58-7.37 (m, 5H), 7.35-7.26 (m, 4H), 7.23-7.18 (m, 1H), 7.14 (d, J=1.5 Hz, 1H), 6.75 (dd, J=1.5, 7.1 Hz, 1H), 4.38 (d, J=5.8 Hz, 2H), 2.51 (s, 3H); 13C NMR (DMSO-d6, 75 MHz) δ 165.5, 162.0, 162.0, 161.3, 140.7, 140.2, 140.0, 139.9, 137.9, 129.6, 128.9, 128.7, 127.7, 127.2, 127.0, 120.9, 103.7, 43.1, 16.9; MS (ES+) m/z 445.0 (M+1).

後処理

  1. temperaturecooled to ambient temperature
  2. filtrationfiltered
  3. customThe solvent was removed in vacuo
  4. dissolutionThe residue was dissolved in dichloromethane (40 mL)
  5. washwashed with saturated aqueous sodium bicarbonate solution (2×20 mL), and brine (20 mL)
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrate in vacuo
  9. customThe residue was recrystallized from ethyl acetate and methanol
  10. customto yield a colorless solid in 20% yield (0.012 g)

出典と根拠

ORDレコード
ord-7326c1c8797b4bc1946991714a7757f9
出典データセット
uspto-grants-2013_09
特許番号
US08541457B2

関連ノート

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