Water → HCID 18918893, compound

HRID 1291264Notes

Reaction equation

HRID 1291264 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]([Cl:23])=[N:19][NH:20][C:21](=[O: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]([Cl:23])=[N:19][N:20]([CH3:28])[C:21](=[O: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 18919214HCID 18919214, compound

Product 1

HCID 18918893HCID 18918893, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The procedure of Example 32 was repeated except that 1-[4-(4-chlorobenzoyl)benzyl]-7-chloroimidazo[4,5-d]pyridazin-4(5H)-one was used as the starting compound. Thus, this starting compound (424 mg) was dissolved in DMF (7 ml) followed by addition of potassium carbonate (465 mg). Then, methyl iodide (0.2 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; ethyl acetate: methanol=1:0-20:1) to provide 218 mg (50%) of the title compound. 1H-NMR (CDCl3) δ: 3.87(3H,s), 5.74(2H,s), 7.23(2H,d,J=8.4Hz), 7.46(2H,d,J=8.4Hz), 7.72(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; ethyl acetate: methanol=1:0-20:1)

Sources & evidence

ORD record
ord-a22d32b691b243beb86f5cf4c23f2bad
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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