Water → 6-(3,5-difluorophenyl)-2-[3-(5-oxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)benzyl]-2H-pyridazin-3-one

HRID 2088363Notes

Reaction equation

HRID 2088363 reaction equation
[CH:1](OC(Cl)(Cl)Cl)=[O:2].[F:8][C:9]1[CH:10]=[C:11]([C:16]2[CH:21]=[CH:20][C:19](=[O:22])[N:18]([CH2:23][C:24]3[CH:25]=[C:26]([CH:31]=[CH:32][CH:33]=3)[C:27]([NH:29][NH2:30])=[O:28])[N:17]=2)[CH:12]=[C:13]([F:15])[CH:14]=1.O>O1CCOCC1>[F:8][C:9]1[CH:10]=[C:11]([C:16]2[CH:21]=[CH:20][C:19](=[O:22])[N:18]([CH2:23][C:24]3[CH:33]=[CH:32][CH:31]=[C:26]([C:27]4[O:28][C:1](=[O:2])[NH:30][N:29]=4)[CH:25]=3)[N:17]=2)[CH:12]=[C:13]([F:15])[CH:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 13647314TrichloromethylformateHCID 595344973-[3-(3,5-difluorophenyl)-6-oxo-6H-pyridazin-1-ylmethyl]benzohydrazide

Product 1

HCID 248302816-(3,5-difluorophenyl)-2-[3-(5-oxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)benzyl]-2H-pyridazin-3-one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

7.2 A solution of 131 mg (0.65 mmol) of trichloromethyl formate in 3 ml of dioxane is added to a suspension of 178 mg (0.50 mmol) of 3-[3-(3,5-di-fluorophenyl)-6-oxo-6H-pyridazin-1-ylmethyl]benzohydrazide in 1 ml of dioxane, and the mixture is heated at the boil for 4 hours. The reaction mixture is allowed to cool, and water is added. The resultant precipitate is filtered off with suction, washed with water and dried. The residue is chromatographed on a silica gel column with dichloromethane/methanol, giving 6-(3,5-difluorophenyl)-2-[3-(5-oxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)benzyl]-2H-pyridazin-3-one (“A15”) as colourless crystals; ESI 383;

Workup

  1. temperaturethe mixture is heated at the boil for 4 hours
  2. temperatureto cool
  3. filtrationThe resultant precipitate is filtered off with suction
  4. washwashed with water
  5. customdried
  6. customThe residue is chromatographed on a silica gel column with dichloromethane/methanol

Sources & evidence

ORD record
ord-cd0637fb4fda4b1ba9bd29e22d1ab2fd
Source dataset
uspto-grants-2013_05
Patent number
US08435981B2

Reaction notes

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