Water → HCID 9800948, compound

HRID 992269Notes

Reaction equation

HRID 992269 reaction equation
CI.[C:3]([C:6]1[C:7]([CH3:28])=[C:8]([S:20][C:21]2[CH:26]=[CH:25]C(N)=[CH:23][CH:22]=2)[C:9](=[O:19])[N:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[N:11]=1)(=[O:5])[CH3:4].N1C(C)=CC=CC=1C.O.[CH3:38][N:39]([CH3:42])[CH:40]=O>>[C:3]([C:6]1[C:7]([CH3:28])=[C:8]([S:20][C:21]2[CH:22]=[CH:23][C:40]([N:39]([CH3:42])[CH3:38])=[CH:25][CH:26]=2)[C:9](=[O:19])[N:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[N:11]=1)(=[O:5])[CH3:4]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 79372,6-LutidineHCID 18412001HCID 18412001, compound

Product 1

HCID 9800948HCID 9800948, compound

Procedure

Methyl iodide (0.9 ml) was added to a solution of 6-acetyl-4-(4-aminophenylthio)-2-(4-fluorophenyl)-5-methyl-3(2H)-pyridazinone (370 mg) and 2,6-lutidine (1 ml) in N,N-dimethylformamide (5 ml) at 5° C., followed by stirring at room temperature for 12 hours. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. After washing with water and a brine, the organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by evaporation, and the resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1), and was crystallized from ether/hexane to obtain 6-acetyl-4-(4-dimethylaminophenylthio)-2-(4-fluorophenyl)-5-methyl-3(2H)-pyridazinone (120 mg) (Compound No. 4-04).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washAfter washing with water
  3. dry with materiala brine, the organic layer was dried over anhydrous magnesium sulfate
  4. customThe solvent was removed by evaporation
  5. customthe resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1)
  6. customwas crystallized from ether/hexane

Sources & evidence

ORD record
ord-1cd40767accd4dd486a7117409b04563
Source dataset
uspto-grants-2002_10
Patent number
US06469003B1

Reaction notes

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