HCID 71269993, compound → HCID 178518792, compound

HRID 927139Notes

Reaction equation

HRID 927139 reaction equation
[CH2:1]([C:8]1[N:13]=[N:12][C:11]([O:14]CC2C=CC=CC=2)=[C:10]([O:22]CC2C=CC=CC=2)[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[Pd]>[CH2:1]([C:8]1[CH:9]=[C:10]([OH:22])[C:11](=[O:14])[NH:12][N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 71269993HCID 71269993, compound2×

Product 1

HCID 178518792HCID 178518792, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a degassed solution of 6-benzyl-3,4-bis(benzyloxy)pyridazine (Intermediate 23: 0.16 g, 0.418 mmol) in methanol (4.18 ml) was added 10% palladium on carbon (0.045 g, 0.042 mmol). The mixture was degassed, evacuated and filled with hydrogen from a balloon. After 1 hour the reaction mixture was degassed and filtered through a pad of “Celite” diatomaceous earth, washing with methanol and concentrated to give a yellow oil. The crude oil was purified by reverse phase chromatography (25 g C18) cartridge eluting with 5-100% acetonitrile/water with acidic modifier and the appropriate fractions combined to give a cream solid (yield=77%).

Workup

  1. customThe mixture was degassed
  2. customevacuated
  3. additionfilled with hydrogen from a balloon
  4. customAfter 1 hour the reaction mixture was degassed
  5. filtrationfiltered through a pad of “Celite” diatomaceous earth
  6. washwashing with methanol
  7. concentrationconcentrated
  8. customto give a yellow oil
  9. customThe crude oil was purified by reverse phase chromatography (25 g C18) cartridge
  10. washeluting with 5-100% acetonitrile/water with acidic modifier

Sources & evidence

ORD record
ord-f06d3d07976b490c8bc246f071bf09d1
Source dataset
uspto-grants-2016_03
Patent number
US09290456B2

Reaction notes

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