Dimethylformamide → N-(2,4-Difluorophenyl)-N'-(4-{[6-methoxy-7-(2-methoxyethoxy)-4-quinolyl]oxy}-2,3-dimethylphenyl) urea

HRID 1375812Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1375812
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[CH:25]=[CH:24][C:23]([NH:26][C:27]([NH:29][C:30]4[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:31]=4[F:37])=[O:28])=[C:22]([CH3:38])[C:21]=3[CH3:39])=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:40][CH3:41])[C:2]1C=CC=CC=1.[H][H].CN(C)[CH:46]=[O:47]>C(N(CC)CC)C.[OH-].[Pd+2].[OH-]>[F:37][C:31]1[CH:32]=[C:33]([F:36])[CH:34]=[CH:35][C:30]=1[NH:29][C:27]([NH:26][C:23]1[CH:24]=[CH:25][C:20]([O:19][C:13]2[C:12]3[C:17](=[CH:18][C:9]([O:8][CH2:1][CH2:2][O:47][CH3:46])=[C:10]([O:40][CH3:41])[CH:11]=3)[N:16]=[CH:15][CH:14]=2)=[C:21]([CH3:39])[C:22]=1[CH3:38])=[O:28]

Komponenten

6

Edukt 3

HCID 6228DimethylformamideHCID 22667195N-(4-{[7-(Benzyloxy)-6-methoxy-4-quinolyl)oxy}-2,3-dimethylphenyl)-N'-(2,4-difluorophenyl)ureaHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 17819598N-(2,4-Difluorophenyl)-N'-(4-{[6-methoxy-7-(2-methoxyethoxy)-4-quinolyl]oxy}-2,3-dimethylphenyl) urea

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9942167Palladium hydroxideKatalysatorHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

N-(4-{[7-(Benzyloxy)-6-methoxy-4-quinolyl]oxy}-2,3-dimethylphenyl)-N′-(2,4-difluorophenyl)urea (213 mg) was dissolved in N,N-dimethylformamide (5 ml) and triethylamine (1 ml), and palladium hydroxide (40 mg) was added to the solution. The mixture was stirred in a hydrogen atmosphere at room temperature overnight. The reaction solution was filtered through Celite and was then washed with chloroform/methanol. The solvent was removed by distillation under the reduced pressure. A 90 mg portion of the residue (184 mg) was dissolved in N,N-dimethylformamide (1.5 ml), and potassium carbonate (32 mg), tetra-n-butylammonium iodide (7 mg), and 2-bromoethyl methyl ether (32 mg) were added to the solution. The mixture was stirred at 70° C. overnight. A saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution, and the mixture was extracted with chloroform. The chloroform layer was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by thin-layer chromatography on silica gel by development with chloroform/acetone (2/1) to give 110 mg of the title compound.

Aufarbeitung

  1. filtrationThe reaction solution was filtered through Celite
  2. washwas then washed with chloroform/methanol
  3. customThe solvent was removed by distillation under the reduced pressure
  4. dissolutionA 90 mg portion of the residue (184 mg) was dissolved in N,N-dimethylformamide (1.5 ml)
  5. additionpotassium carbonate (32 mg), tetra-n-butylammonium iodide (7 mg), and 2-bromoethyl methyl ether (32 mg) were added to the solution
  6. additionA saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution
  7. extractionthe mixture was extracted with chloroform
  8. dry with materialThe chloroform layer was dried over anhydrous magnesium sulfate
  9. customThe solvent was removed by distillation under the reduced pressure
  10. customThe residue was purified by thin-layer chromatography on silica gel by development with chloroform/acetone (2/1)

Quellen und Nachweise

ORD-Eintrag
ord-29de97ca59be4e0e973b9cd6fa4b3947
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07169789B2

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