Ethanol heptane → HCID 178518822, compound

HRID 927128Notes

Reaction equation

HRID 927128 reaction equation
C([O:8][C:9]1[N:10]=[N:11][C:12]([C:23]#[C:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][N:26]=2)=[CH:13][C:14]=1[O:15]CC1C=CC=CC=1)C1C=CC=CC=1.C(O)C.CCCCCCC>C(O)C.[Pd]>[OH:15][C:14]1[C:9](=[O:8])[NH:10][N:11]=[C:12]([CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:32])([F:33])[F:34])=[CH:27][N:26]=2)[CH:13]=1

Participants

5

Reactant 2

HCID 22502148Ethanol heptaneHCID 712699103,4-Bis(benzyloxy)-6-{[5-(trifluoromethyl)pyridin-2-yl]ethynyl}pyridazine2×

Product 1

HCID 178518822HCID 178518822, compoundYield 48.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3,4-bis(benzyloxy)-6-{[5-(trifluoromethyl)pyridin-2-yl]ethynyl}pyridazine (Intermediate 6; 460 mg, 0.997 mmol) was dissolved in ethanol and palladium on carbon was added before the mixture was purged and subjected to hydrogen gas. On completion of the reaction the solvent was removed in vacuo to yield a residue which was purified by reverse phase chromatography using 5-90% acetonitrile in acidic water (0.05% trifluoroacetic acid) to give, after recrystallisation from an ethanol-heptane mixture, 4-hydroxy-6-(2-(5-(trifluoromethyl)pyridin-2-yl)ethyl)pyridazin-3(2H)-one (136 mg, 0.48 mmol, 48% yield).

Workup

  1. customwas purged
  2. customOn completion of the reaction the solvent
  3. customwas removed in vacuo
  4. customto yield a residue which
  5. customwas purified by reverse phase chromatography
  6. customto give

Sources & evidence

ORD record
ord-bbf329ae4b3c45a2ad0ad8a0cce8c7b7
Source dataset
uspto-grants-2016_03
Patent number
US09290456B2

Reaction notes

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