Cesium carbonate → N-Benzyl-4-methyl-2-(2-oxo-4-((5-phenyl-1,3,4-oxadiazol-2-yl)methoxy)pyridin-1(2H)-yl)thiazole-5-carboxamide

HRID 1887337

Reaktionsgleichung

Reaktionsgleichung von HRID 1887337
[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([N:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][C:17]2=[O:23])=[N:13][C:12]=1[CH3:24])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:32][C:33]1[O:34][C:35]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[N:36][N:37]=1>CN(C)C=O>[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([N:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:32][C:33]3[O:34][C:35]([C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=4)=[N:36][N:37]=3)=[CH:18][C:17]2=[O:23])=[N:13][C:12]=1[CH3:24])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 3149412-(Chloromethyl)-5-phenyl-1,3,4-oxadiazoleHCID 54742338N-benzyl-2-(4-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamide

Produkt 1

HCID 57744445N-Benzyl-4-methyl-2-(2-oxo-4-((5-phenyl-1,3,4-oxadiazol-2-yl)methoxy)pyridin-1(2H)-yl)thiazole-5-carboxamideAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of N-benzyl-2-(4-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamide (0.20 g, 0.58 mmol) in anhydrous N,N-dimethylformamide (8 mL) was added cesium carbonate (0.32 g, 0.99 mmol) and catalytic amount of n-tetrabutylammonium iodide, followed by the addition of 2-(chloromethyl)-5-phenyl-1,3,4-oxadiazole (0.15 g, 0.76 mmol). The reaction mixture was heated at 80° C. for 20 hours and concentrated in vacuo, followed by the addition of dichloromethane (100 mL). The mixture was washed with water (70 mL). The organic layer was dried over anhydrous sodium sulfate and filtered. The solvent was concentrated in vacuo. The residue was recrystallized in ethyl acetate and hexane. The solid was collected by filtration and washed with methanol and hexanes to afford the title compound as a colorless solid in 38% yield (0.11 g): 1H NMR (300 MHz, DMSO-d6) δ 8.84 (t, J=5.9 Hz, 1H), 8.69 (d, J=8.0 Hz, 1H), 8.04-8.01 (m, 2H), 7.69-7.57 (m, 3H), 7.37-7.29 (m, 4H), 7.27-7.21 (m, 1H), 6.50-6.43 (m, 2H), 5.64 (s, 2H), 4.42 (d, J=5.9 Hz, 2H), 2.58 (s, 3H); MS (ES+) m/z 500.2 (M+1), 522.2 (M+23).

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. additionfollowed by the addition of dichloromethane (100 mL)
  3. washThe mixture was washed with water (70 mL)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe solvent was concentrated in vacuo
  7. customThe residue was recrystallized in ethyl acetate
  8. filtrationThe solid was collected by filtration
  9. washwashed with methanol and hexanes

Quellen und Nachweise

ORD-Eintrag
ord-28165492c80c4f76ad3ebbb1b5850879
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501746B2

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