Hydrogen Peroxide → HCID 22106390, compound

HRID 1456385Notes

Reaction equation

HRID 1456385 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][N:14]=2)[C:9]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=2)=[C:8]([NH:24][C:25]([NH:27][C:28]2[C:33]([CH:34]([CH3:36])[CH3:35])=[CH:32][CH:31]=[CH:30][C:29]=2[CH:37]([CH3:39])[CH3:38])=[O:26])[C:7]1=[O:40])#[N:2].C(=O)([O-])[O-:42].[Na+].[Na+].OO.O>CO.CC(C)=O>[NH2:2][C:1]([CH2:3][CH2:4][CH2:5][N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][N:14]=2)[C:9]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=2)=[C:8]([NH:24][C:25]([NH:27][C:28]2[C:29]([CH:37]([CH3:39])[CH3:38])=[CH:30][CH:31]=[CH:32][C:33]=2[CH:34]([CH3:36])[CH3:35])=[O:26])[C:7]1=[O:40])=[O:42]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 10340Sodium CarbonateHCID 22105924HCID 22105924, compound

Product 1

HCID 22106390HCID 22106390, compound

Reagents, catalysts & solvents 1

HCID 21894497Aceton-methanolSolvent

Procedure

To a solution of N-[1-(3-cyanopropyl)-4-(3-methoxyphenyl)-l,2-dihydro-2-oxo-1,8-naphthyridin-3-yl]-N'-(2,6-diisopropylphenyl)urea (100 mg, 0.19 mmol) in methanol-acetone (3 ml) were added 10% aqueous sodium carbonate solution (1 ml) and 30% hydrogen peroxide (1 ml), and the mixture was stirred at room temperature for three hours. The mixture was poured into water, and extracted with ethyl acetate. The extract was washed with a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The residue was concentrated under reduced pressure, and purified by preparative thin layer chromatography to give the title compound (96 mg, 0.17 mmol).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationThe residue was concentrated under reduced pressure
  5. custompurified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-57fccbaa62bc4b68a5c29fe1fd59b9e4
Source dataset
uspto-grants-1998_12
Patent number
US05843957

Reaction notes

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