Dimethylformamide → HCID 22667196, compound

HRID 1375904Notes

Reaction equation

HRID 1375904 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-methoxyphenyl}-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-07c5f1ff15b9421b821028ea5088113f
Source dataset
uspto-grants-2007_01
Patent number
US07169789B2

Reaction notes

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