Dimethylformamide → HCID 67268082, compound

HRID 598134Notes

Reaction equation

HRID 598134 reaction equation
[Cl:1][C:2]1[C:3]2[CH:11]=[CH:10][N:9]([C:12]3[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][C:13]=3[CH3:19])[C:4]=2[C:5](=[O:8])[NH:6][N:7]=1.CI.[C:22](=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[Cl:1][C:2]1[C:3]2[CH:11]=[CH:10][N:9]([C:12]3[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][C:13]=3[CH3:19])[C:4]=2[C:5](=[O:8])[N:6]([CH3:22])[N:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 67266813HCID 67266813, compound

Product 1

HCID 67268082HCID 67268082, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-chloro-1-(2,4-dimethylphenyl)-1,6-dihydro-7H-pyrrolo[2,3-d]pyridazin-7-one (0.30 g, 1.10 mmol), MeI (0.075 ml, 1.21 mmol), potassium carbonate (0.30 g, 2.2 mmol) and DMF (5 ml) was stirred at room temperature for 13 hours. The mixture was diluted with water (50 ml) and extracted with ethyl acetate (50 ml×2). The extracts were combined, washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with hexane/ethyl acetate (5:1) to give 0.31 g (98%) of the title compound as crystals.

Workup

  1. extractionextracted with ethyl acetate (50 ml×2)
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with hexane/ethyl acetate (5:1)

Sources & evidence

ORD record
ord-bdfe5a426eea4276b7f3619a0ea3bce3
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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