Chloromethyl Methyl Ether → HCID 22667091, compound

HRID 1375862

Reaction equation

HRID 1375862 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:4][C:3]=1[NH:23][C:24]([NH:26][CH2:27][CH2:28][CH3:29])=[O:25].[H-].[Na+].[CH3:32][O:33][CH2:34]Cl>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:4][C:3]=1[N:23]([CH2:32][O:33][CH3:34])[C:24]([NH:26][CH2:27][CH2:28][CH3:29])=[O:25]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 9549295Krn-633

Product 1

HCID 22667091HCID 22667091, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-{2-Chloro-4-[(6,7-dimethoxy-4-quinazolinyl)oxy]-phenyl}-N′-propylurea 100 mg) was dissolved in anhydrous tetrahydrofuran (30 ml), and sodium hydride (60 wt %, 88 mg) was added to the solution. The mixture was stirred at room temperature for 15 min. Next, chloromethyl methyl ether (67 μl) was added to the reaction solution, and the mixture was stirred at room temperature for additional 30 min. The solvent was removed by distillation under the reduced pressure, and water was added to the residue. The mixture was extracted with chloroform. The chloroform layer was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by HPLC by development with chloroform/methanol to give 18 mg (yield 18%) of the title compound.

Workup

  1. stirringthe mixture was stirred at room temperature for additional 30 min
  2. customThe solvent was removed by distillation under the reduced pressure, and water
  3. additionwas added to the residue
  4. extractionThe mixture was extracted with chloroform
  5. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
  6. customThe solvent was removed by distillation under the reduced pressure
  7. customThe residue was purified by HPLC by development with chloroform/methanol

Sources & evidence

ORD record
ord-8a09e0ed77954c17b69c51b37a7ddf92
Source dataset
uspto-grants-2007_01
Patent number
US07169789B2

Linked notes

Loading…