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

HRID 45385

반응식

HRID 45385 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
130 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-7326c1c8797b4bc1946991714a7757f9
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541457B2

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