Water → HCID 18919035, compound

HRID 1291263Notes

Reaction equation

HRID 1291263 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([C:6]([C:8]2[CH:25]=[CH:24][C:11]([CH2:12][N:13]3[C:17]4[C:18](=[O:23])[NH:19][N:20]=[C:21]([Cl:22])[C:16]=4[N:15]=[CH:14]3)=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[C:28](=O)([O-])[O-].[K+].[K+].CI.O>CN(C=O)C>[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([C:6]([C:8]2[CH:25]=[CH:24][C:11]([CH2:12][N:13]3[C:17]4[C:18](=[O:23])[N:19]([CH3:28])[N:20]=[C:21]([Cl:22])[C:16]=4[N:15]=[CH:14]3)=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 18918884HCID 18918884, compound

Product 1

HCID 18919035HCID 18919035, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In DMF (15 ml) was dissolved 1-[4-(4-chlorobenzoyl)benzyl]-4-chloroimidazo[4,5-d]pyridazin-7(6H)-one (963 mg) followed by addition of potassium carbonate (985 mg). Then, methyl iodide (0.45 ml) was added and the mixture was stirred at room temperature for 65 hours. To this reaction mixture was added water (50 ml) and the resulting crystals were harvested by filtration. This crystal crop was purified by silica gel column chromatography (stationary phase 30 g; dichloromethane: ether=1:0-3:1) to provide 655 mg (66%) of the title compound. 1H-NMR (CDCl3) δ: 3.86(3H,s), 5.81(2H,s), 7.45(2H,d,J=7.8Hz), 7.46(2H,d,J=8.6Hz), 7.73(2H,d,J=8.6Hz), 7.78(2H,d,J=8.2Hz), 8.01(1H,s).

Workup

  1. filtrationthe resulting crystals were harvested by filtration
  2. customThis crystal crop was purified by silica gel column chromatography (stationary phase 30 g; dichloromethane: ether=1:0-3:1)

Sources & evidence

ORD record
ord-dfe10f9456f8483498687acb94fd2934
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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