Water → HCID 18919163, compound

HRID 1291290Notes

Reaction equation

HRID 1291290 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]2[CH:9]=[CH:10][NH:11][C:5]=2[CH:4]=[N:3]1.[H-].[Na+].[Cl:14][C:15]1[CH:30]=[CH:29][C:18]([C:19]([C:21]2[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=2)[CH2:24]Br)=[O:20])=[CH:17][CH:16]=1.O>CN(C=O)C>[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([C:19]([C:21]2[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=2)[CH2:24][N:11]2[C:5]3[CH:4]=[N:3][N:2]([CH3:1])[C:7](=[O:8])[C:6]=3[CH:9]=[CH:10]2)=[O:20])=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 136496533-(4-Chlorobenzoyl)benzyl bromideHCID 1356675915-Methyl-1H-pyrrolo[2,3-d]pyridazin-4(5H)-one

Product 1

HCID 18919163HCID 18919163, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 5-methyl-1H-pyrrolo[2,3-d]pyridazin-4(5H)-one (298 mg) in DMF (10 ml) was dripped into a suspension of 60% sodium hydride-oil (96 mg) in DMF (8 ml) on an ice-water bath. The mixture was stirred at room temperature for 1 hour, after which a solution of 3-(4-chlorobenzoyl)benzyl bromide (681 mg) in DMF (15 ml) was added and the mixture was further stirred at room temperature for 2 hours. The reaction was stopped by adding water and the reaction mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (developer; n-hexane: ethyl-acetate=1:3) to provide the title compound as white powder (630 mg, yield 83%).

Workup

  1. stirringthe mixture was further stirred at room temperature for 2 hours
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (developer; n-hexane: ethyl-acetate=1:3)

Sources & evidence

ORD record
ord-9426a3000bec46b1a1bc1d38103b6df1
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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