Hydrochloric Acid → HCID 18411996, compound

HRID 992266Notes

Reaction equation

HRID 992266 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[C:12]([O:15][CH2:16][C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)=[C:11]([CH3:23])[C:10]([C:24]3([CH3:29])OCC[O:25]3)=[N:9]2)=[CH:4][CH:3]=1.[ClH:30]>>[ClH:30].[C:24]([C:10]1[C:11]([CH3:23])=[C:12]([O:15][CH2:16][C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[C:13](=[O:14])[N:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[N:9]=1)(=[O:25])[CH3:29]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 18412008HCID 18412008, compound

Product 1

HCID 18411996HCID 18411996, compound

Procedure

To a solution of 2-(4-fluorophenyl)-5-methyl-6-(2-methyl-1,3-dioxolan-2-yl)-4-(3-pyridylmethoxy)-3(2H)-pyridazinone (320 mg) in N,N-tetrahydrofuran (12 ml) was added 6N hydrochloric acid (1.4 ml), followed by stirring at room temperature for 17 hours. The solvent was removed by evaporation, a saturated aqueous sodium hydrogen carbonate solution was added to the resulting residue to adjust the pH to about 10 and then the mixture was extracted with chloroform. After washing with water and a brine, the organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by evaporation, and a 4M hydrogen chlorid/1,4-dioxane solution (10 ml) was added to the resulting residue, followed by stirring at room temperature for 10 minutes. The solvent was removed by evaporation, and the resulting residue was crystallized from ether to obtain 6-acetyl-2-(4-fluorophenyl)-5-methyl-4-(3-pyridylmethoxy)-3(2H)-pyridazinone hydrochloride (190 mg) (Compound No. 1-114).

Workup

  1. customThe solvent was removed by evaporation
  2. additiona saturated aqueous sodium hydrogen carbonate solution was added to the resulting residue
  3. extractionthe mixture was extracted with chloroform
  4. washAfter washing with water
  5. dry with materiala brine, the organic layer was dried over anhydrous magnesium sulfate
  6. customThe solvent was removed by evaporation
  7. additiona 4M hydrogen chlorid/1,4-dioxane solution (10 ml) was added to the resulting residue
  8. stirringby stirring at room temperature for 10 minutes
  9. customThe solvent was removed by evaporation
  10. customthe resulting residue was crystallized from ether

Sources & evidence

ORD record
ord-dc45a7d4fc84455da59e606685c306df
Source dataset
uspto-grants-2002_10
Patent number
US06469003B1

Reaction notes

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