Dimethylformamide → HCID 22667196, compound

HRID 1008469Notes

Reaction equation

HRID 1008469 reaction equation
BrCC[CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[O:16][CH3:17])[N:12]=[CH:11][N:10]=[C:9]2[O:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26]([NH:28][CH2:29][CH2:30][CH3:31])=[O:27])=[C:21](Cl)[CH:20]=1.[C:33](=[O:36])([O-])[O-].[K+].[K+].[CH3:39][N:40]1[CH2:45][CH2:44]N[CH2:42][CH2:41]1.CN(C)[CH:48]=[O:49]>>[CH3:48][O:49][C:21]1[CH:20]=[C:19]([O:18][C:9]2[C:8]3[C:13](=[CH:14][C:15]([O:16][CH2:17][CH2:42][CH2:41][N:40]4[CH2:39][CH2:33][O:36][CH2:44][CH2:45]4)=[C:6]([O:5][CH3:4])[CH:7]=3)[N:12]=[CH:11][N:10]=2)[CH:24]=[CH:23][C:22]=1[NH:25][C:26]([NH:28][CH2:29][CH2:30][CH3:31])=[O:27]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 22667049HCID 22667049, compound

Product 1

HCID 22667196HCID 22667196, compoundYield 42%

Procedure

N-4-[(7-Hydroxy-6-methoxy-4-quinazolinyl)oxy]-2-methoxyphenyl}-N′-propylurea (100 mg), potassium carbonate (138 mg), and 1,3-dibromopropane (56 mg) were dissolved in N,N-dimethylformamide (5 ml), and the solution was stirred at room temperature for 3 hr. The solvent was removed by distillation under the reduced pressure. Water was added to the residue, and the mixture was extracted with chloroform/2-propanol (4/1). The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed by distillation under the reduced pressure. The residue was washed with ether to give 53 mg (yield 41%) of N-(4-[7-(3-bromopropoxy)-6-methoxy-4-quinazolinyl]oxy-2-methoxy-phenyl}-N′-propylurea. N-(4-{[6-(3-Bromopropoxy)-7-methoxy-4-quinazolinyl]oxy}-2-chlorophenyl}-N′-propylurea (50 mg), potassium carbonate (60 mg), and N-methylpiperazine (100 μl) were dissolved in N,N-dimethylformamide (2 ml), and the solution was stirred at room temperature for 16 hr. The solvent was removed by distillation under the reduced pressure. A saturated aqueous sodium hydrogencarbonate solution was added to the residue, and the mixture was extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed by distillation under the reduced pressure. The residue was purified by chromatography on silica gel by development with chloroform/methanol to give 22 mg (yield 42%) of the title compound.

Workup

  1. customThe solvent was removed by distillation under the reduced pressure
  2. additionA saturated aqueous sodium hydrogencarbonate solution was added to the residue
  3. extractionthe mixture was extracted with chloroform
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was removed by distillation under the reduced pressure
  6. customThe residue was purified by chromatography on silica gel by development with chloroform/methanol

Sources & evidence

ORD record
ord-7bc0c1554a6c46dd8c5b2a578757470c
Source dataset
uspto-grants-2004_09
Patent number
US06797823B1

Reaction notes

Loading…