Dimethylformamide → HCID 69353429, compound

HRID 1375814Notes

Reaction equation

HRID 1375814 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[C:25]([CH3:26])=[CH:24][C:23]([NH:27][C:28]([NH:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=4[O:37][CH3:38])=[O:29])=[C:22]([CH3:39])[CH:21]=3)=[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]>[OH-].[Pd+2].[OH-]>[CH3:41][O:40][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][C:9]=1[O:8][CH2:1][CH2:2][O:47][CH3:46])[N:16]=[CH:15][CH:14]=[C:13]2[O:19][C:20]1[C:25]([CH3:26])=[CH:24][C:23]([NH:27][C:28]([NH:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[O:37][CH3:38])=[O:29])=[C:22]([CH3:39])[CH:21]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 22667160HCID 22667160, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69353429HCID 69353429, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 9942167Palladium hydroxideCatalyst

Conditions

Temperature
70 °C

Procedure

N-(4-{[7-(Benzyloxy)-6-methoxy-4-quinolyl]oxy}-2,5-dimethylphenyl)-N′-(2-methoxyphenyl)urea (363 mg) was dissolved in N,N-dimethylformamide (6 ml), and palladium hydroxide (363 mg) was added to the solution. The mixture was stirred in a hydrogen atmosphere at room temperature overnight. The solvent was removed by distillation under the reduced pressure, and the residue was dissolved in chloroform and methanol. The solution was filtered through Celite. Next, the solvent was removed by distillation under the reduced pressure. The residue (191 mg), potassium carbonate (110 mg), tetra-n-butylammonium iodide (12 mg), and 2-bromoethyl methyl ether (80 mg) were dissolved in N,N-dimethylformamide (5 ml), and the solution was stirred at 70° C. overnight. The solvent was removed by distillation under the reduced pressure. Water was added to the residue, and the mixture was extracted with chloroform. The chloroform layer was dried over sodium 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/methanol (10/1) to give 128 mg (yield 76%) of the title compound.

Workup

  1. customThe solvent was removed by distillation under the reduced pressure
  2. dissolutionthe residue was dissolved in chloroform
  3. filtrationThe solution was filtered through Celite
  4. customNext, the solvent was removed by distillation under the reduced pressure
  5. dissolutionThe residue (191 mg), potassium carbonate (110 mg), tetra-n-butylammonium iodide (12 mg), and 2-bromoethyl methyl ether (80 mg) were dissolved in N,N-dimethylformamide (5 ml)
  6. customThe solvent was removed by distillation under the reduced pressure
  7. additionWater was added to the residue
  8. extractionthe mixture was extracted with chloroform
  9. dry with materialThe chloroform layer was dried over sodium sulfate
  10. customThe solvent was removed by distillation under the reduced pressure
  11. customThe residue was purified by thin-layer chromatography on silica gel by development with chloroform/methanol (10/1)

Sources & evidence

ORD record
ord-ee8744516f444aa18e3c67e39f8a35de
Source dataset
uspto-grants-2007_01
Patent number
US07169789B2

Reaction notes

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