Water → HCID 18467162, compound

HRID 2229400Notes

Reaction equation

HRID 2229400 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]([CH2:36]Br)=[CH:29][C:28]=2[CH:38]([CH3:40])[CH3:39])=[O:25])[C:6]1=[O:41])[CH2:2][CH2:3][CH3:4].C1(=O)[NH:46]C(=O)C2=CC=CC=C12.[K].O>CN(C)C=O>[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]([CH2:36][NH2:46])=[CH:29][C:28]=2[CH:38]([CH3:40])[CH3:39])=[O:25])[C:6]1=[O:41])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 18467085HCID 18467085, compoundHCID 24194345Phthalimide potassium salt

Product 1

HCID 18467162HCID 18467162, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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-bromomethylphenyl)urea (400 mg, 0.65 mmol) in dimethylformamide (10 ml) is added potassium phthalimide (144 mg, 0.78 mmol) at room temperature, and the mixture is stirred at room temperature for 3 hours. To the mixture is added water, and the mixture is extracted with ethyl acetate. The organic layer is washed twice with water, and dried over anhydrous magnesium sulfate. The solvent is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography to give the title compound (393 mg, 0.57 mmol) as colorless amorphous.

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washThe organic layer is washed twice with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationThe solvent is concentrated under reduced pressure
  5. customthe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a07322ed100e4cc08a14fd5735ff398c
Source dataset
uspto-grants-2002_07
Patent number
US06420381B1

Reaction notes

Loading…