Water → HCID 18467081, compound

HRID 2229397Notes

Reaction equation

HRID 2229397 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][CH3:22])[CH:16]=2)=[C:7]([NH:23][C:24]([NH:26][C:27]2[C:32]([CH:33]([CH3:35])[CH3:34])=[CH:31][C:30]([O:36]C(=O)C3C=CC=C(Cl)C=3)=[CH:29][C:28]=2[CH:46]([CH3:48])[CH3:47])=[O:25])[C:6]1=[O:49])[CH2:2][CH2:3][CH3:4].C[O-].[Na+].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][CH3:22])[CH:16]=2)=[C:7]([NH:23][C:24]([NH:26][C:27]2[C:32]([CH:33]([CH3:35])[CH3:34])=[CH:31][C:30]([OH:36])=[CH:29][C:28]=2[CH:46]([CH3:48])[CH3:47])=[O:25])[C:6]1=[O:49])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 18467096HCID 18467096, compound

Product 1

HCID 18467081HCID 18467081, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-[1-butyl-4-(3-methoxyphenyl)-1,2-dihydro-2-oxo-1,8-naphthyridin-3-yl]-N′-[2,6-diisopropyl-4-(3-chlorobenzoyloxy)-phenyl]urea (1.0 g, 1.6 mmol) in methanol (30 ml) is added dropwise a 28% sodium methoxide (0.45 ml, 1.76 mmol) at room temperature, and the mixture is stirred at the same temperature for one hour. To the mixture is added water, and the mixture is extracted with ethyl acetate. The extract is washed with an aqueous ammonium chloride solution and a saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (1% methanol/chloroform→2% methanol/chloroform) to give the title compound (0.79 g, 1.45 mmol) as amorphous.

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washThe extract is washed with an aqueous ammonium chloride solution
  3. dry with materiala saturated brine, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue is purified by silica gel column chromatography (1% methanol/chloroform→2% methanol/chloroform)

Sources & evidence

ORD record
ord-b17da5524acf4962ad5f7b0d2cb4a961
Source dataset
uspto-grants-2002_07
Patent number
US06420381B1

Reaction notes

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