HCID 86677036, compound → HCID 178518820, compound

HRID 927181Notes

Reaction equation

HRID 927181 reaction equation
C([O:8][C:9]1[N:10]=[N:11][C:12](/[CH:23]=[CH:24]/[C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[C:27]([C:35]([F:38])([F:37])[F:36])[CH:26]=2)=[CH:13][C:14]=1[O:15]CC1C=CC=CC=1)C1C=CC=CC=1>C1COCC1.[Pd]>[F:38][C:35]([F:36])([F:37])[C:27]1[CH:26]=[C:25]([CH2:24][CH2:23][C:12]2[CH:13]=[C:14]([OH:15])[C:9](=[O:8])[NH:10][N:11]=2)[CH:30]=[CH:29][C:28]=1[C:31]([F:32])([F:34])[F:33]

Participants

4

Reactant 1

HCID 86677036HCID 86677036, compound2×

Product 1

HCID 178518820HCID 178518820, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3,4-bis(benzyloxy)-6-[(E)-2-[3,4-bis(trifluoromethyl)phenyl]-ethenyl]pyridazine (Intermediate 73, 227 mg, 0.428 mmol) in THF (4279 μl) was added palladium on carbon (45.5 mg, 0.043 mmol) and the reaction vessel evacuated and purged with nitrogen (×3). The reaction was stirred under a hydrogen atmosphere for 4 hours and the resulting mixture was filtered through a short pad of diatomacious earth and concentrated in vacuo. The residue was purified by chromatography (C18 silica cartridge eluting with 0-50% acetonitrile in water with basic modifier). The appropriate fractions were combined and concentrated to remove the organics and the aqueous fractions were acidified with hydrochloric acid (2 N) and extracted with ethyl acetate (×2), dried (MgSO4) and concentrated in vacuo to yield 6-{2-[3,4-bis(trifluoromethyl)phenyl]ethyl}-4-hydroxy-2,3-dihydropyridazin-3-one as a cream solid (39 mg, 26%)

Workup

  1. customthe reaction vessel evacuated
  2. custompurged with nitrogen (×3)
  3. filtrationthe resulting mixture was filtered through a short pad of diatomacious earth
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography (C18 silica cartridge
  6. washeluting with 0-50% acetonitrile in water with basic modifier)
  7. concentrationconcentrated
  8. customto remove the organics and the aqueous fractions
  9. extractionextracted with ethyl acetate (×2)
  10. dry with materialdried (MgSO4)
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-10c0afdb3ad14b0c8b23ef6813ad0515
Source dataset
uspto-grants-2016_03
Patent number
US09290456B2

Reaction notes

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