Sodium hydride → HCID 18919022, compound

HRID 1291282Notes

Reaction equation

HRID 1291282 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]2[CH2:9][CH2:10][CH2:11][NH:12][C:5]=2[CH:4]=[N:3]1.[H-].[Na+].[Cl:15][C:16]1[CH:31]=[CH:30][C:19]([C:20]([C:22]2[CH:29]=[CH:28][C:25]([CH2:26]Br)=[CH:24][CH:23]=2)=[O:21])=[CH:18][CH:17]=1>CN(C=O)C.O>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([C:20]([C:22]2[CH:29]=[CH:28][C:25]([CH2:26][N:12]3[C:5]4[CH:4]=[N:3][N:2]([CH3:1])[C:7](=[O:8])[C:6]=4[CH2:9][CH2:10][CH2:11]3)=[CH:24][CH:23]=2)=[O:21])=[CH:30][CH:31]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 98396514-(4-Chlorobenzoyl)benzyl bromideHCID 18918833HCID 18918833, compound

Product 1

HCID 18919022HCID 18919022, compoundYield 59.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In DMF (5 ml) was dissolved 6-methyl-1,2,3,4-tetrahydropyrido[2,3-d]pyridazin-5(6H)-one (116 mg) followed by addition of sodium hydride (60%) (56 mg), and the mixture was stirred at room temperature for 30 minutes. Then, 4-(4-chlorobenzoyl)benzyl bromide (341 mg) was added and the mixture was further stirred at room temperature for 1 hour. This reaction mixture was diluted with water and extracted with ethyl acetate-THF. The organic layer was serially washed with water and saturated aqueous NaCl solution, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel chromatography (ethyl acetate) to provide 165 mg of the title compound as yellow amorphous solid.

Workup

  1. stirringthe mixture was further stirred at room temperature for 1 hour
  2. extractionextracted with ethyl acetate-THF
  3. washThe organic layer was serially washed with water and saturated aqueous NaCl solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-650c04555ce945c7a5a12d5cc75b5a2e
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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