HCID 22936261, compound → HCID 22936426, compound

HRID 853443Notes

Reaction equation

HRID 853443 reaction equation
[CH:1]1([NH:4][C:5]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]3[C:24]4[C:19](=[CH:20][C:21]([O:29][CH3:30])=[C:22]([C:25]([O:27]C)=[O:26])[CH:23]=4)[N:18]=[CH:17][CH:16]=3)=[CH:10][C:9]=2[CH3:31])=[O:6])[CH2:3][CH2:2]1>CO.[OH-].[Na+]>[CH:1]1([NH:4][C:5]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]3[C:24]4[C:19](=[CH:20][C:21]([O:29][CH3:30])=[C:22]([C:25]([OH:27])=[O:26])[CH:23]=4)[N:18]=[CH:17][CH:16]=3)=[CH:10][C:9]=2[CH3:31])=[O:6])[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 22936261HCID 22936261, compound

Product 1

HCID 22936426HCID 22936426, compoundYield 58.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
60 °C

Procedure

After dissolving N-cyclopropyl-N′-[2-methyl-4-(6-methoxycarbonyl-7-methoxy-4-quinolyl)oxyphenyl]urea (173 mg, 0.3972 mmol) in methanol (3 ml), 2N aqueous sodium hydroxide (1 ml) was added and the mixture was heated and stirred at 60° C. for 45 minutes. The solvent was distilled off under reduced pressure, the precipitated crystals were redissolved in methanol, and then 1N hydrochloric acid was added to pH 4 and saturated brine was further added. After extraction with ethyl acetate/tetrahydrofuran, the extract was washed with saturated brine and dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the obtained crystals were suspended in acetone/diethyl ether and then filtered out and dried by aspiration to obtain the title compound (95 mg, 0.2332 mmol, 56.80%) as brown crystals.

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. distillationThe solvent was distilled off under reduced pressure
  4. dissolutionthe precipitated crystals were redissolved in methanol
  5. addition1N hydrochloric acid was added to pH 4 and saturated brine
  6. additionwas further added
  7. extractionAfter extraction with ethyl acetate/tetrahydrofuran
  8. washthe extract was washed with saturated brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. distillationthe solvent was distilled off under reduced pressure
  11. filtrationfiltered out
  12. customdried by aspiration

Sources & evidence

ORD record
ord-767f85199711477ba2dd3d1945037466
Source dataset
uspto-grants-2007_08
Patent number
US07253286B2

Reaction notes

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