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

HRID 1008385Notes

Reaction equation

HRID 1008385 reaction equation
[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][CH:33]=[CH:32][C:31]=4[O:36][CH3:37])=[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-]>[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[CH:25]=[CH:24][C:23]([NH:26][C:27]([NH:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[O:36][CH3:37])=[O:28])=[C:22]([CH3:38])[C:21]=1[CH3:39]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 22667072N-(4-{[7-(Benzyloxy)-6-methoxy-4-quinolyl]oxy}-2,3-dimethylphenyl)-N'-(2-methoxyphenyl)-ureaHCID 178418361HCID 178418361, compound

Product 1

HCID 22667149N-(4-{[6-Methoxy-7-(2-methoxyethoxy)-4-quinolyl]oxy}-2,3-dimethylphenyl)-N'-(2-methoxyphenyl)urea

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
70 °C

Procedure

N-(4-{[7-(Benzyloxy)-6-methoxy-4-quinolyl]oxy}-2,3-dimethylphenyl)-N′-(2-methoxyphenyl)urea (161 mg) was dissolved in N,N-dimethylformamide (4 ml) and triethylamine (1 ml), and palladium hydroxide (32 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 washed with chloroform/methanol. The solvent was removed by distillation under the reduced pressure. A 110 mg portion of the residue (223 mg) was dissolved in N,N-dimethylformamide (1.5 ml), and potassium carbonate (23 mg), tetra-n-butylammonium iodide (5 mg), and 2-bromoethyl methyl ether (23 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 89 mg of the title compound.

Workup

  1. filtrationThe reaction solution was filtered through Celite
  2. washwas washed with chloroform/methanol
  3. customThe solvent was removed by distillation under the reduced pressure
  4. dissolutionA 110 mg portion of the residue (223 mg) was dissolved in N,N-dimethylformamide (1.5 ml)
  5. additionpotassium carbonate (23 mg), tetra-n-butylammonium iodide (5 mg), and 2-bromoethyl methyl ether (23 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)

Sources & evidence

ORD record
ord-863ee4a556a74dd29a75f2acb280fb77
Source dataset
uspto-grants-2004_09
Patent number
US06797823B1

Reaction notes

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