Water → HCID 22106202, compound

HRID 1456377Notes

Reaction equation

HRID 1456377 reaction equation
[CH2:1]([N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][N:13]=2)[C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:22][CH2:23][O:24]C(=O)C)[CH:16]=2)=[C:7]([NH:28][C:29]([NH:31][C:32]2[C:37]([CH:38]([CH3:40])[CH3:39])=[CH:36][CH:35]=[CH:34][C:33]=2[CH:41]([CH3:43])[CH3:42])=[O:30])[C:6]1=[O:44])[CH2:2][CH2:3][CH3:4].C(=O)([O-])[O-].[K+].[K+].O>CO>[CH2:1]([N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][N:13]=2)[C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:22][CH2:23][OH:24])[CH:16]=2)=[C:7]([NH:28][C:29]([NH:31][C:32]2[C:37]([CH:38]([CH3:39])[CH3:40])=[CH:36][CH:35]=[CH:34][C:33]=2[CH:41]([CH3:43])[CH3:42])=[O:30])[C:6]1=[O:44])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 22106211HCID 22106211, compound

Product 1

HCID 22106202HCID 22106202, compoundYield 78.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-[1-butyl-4-{3-(2-acetoxyethoxy)phenyl}-1,2-dihydro-2-oxo-1,8-naphthyridin-3-yl]-N'-(2,6-diisopropylphenyl)urea (196 mg, 0.33 mmol) in methanol (10 ml) was added potassium carbonate (11 mg), and the mixture was stirred at room temperature for 4 hours. To the mixture was added water, and the mixture was extracted with ethyl acetate. The extract was washed with water, washed with a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The residue was concentrated under reduced pressure, and crystallized from ether/hexane to give the title compound (145 mg, 0.26 mmol).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. washwashed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationThe residue was concentrated under reduced pressure
  6. customcrystallized from ether/hexane

Sources & evidence

ORD record
ord-73eee8cf1c53490d8b7e7f6ce2deaadc
Source dataset
uspto-grants-1998_12
Patent number
US05843957

Reaction notes

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