HCID 67373515, compound → HCID 136386260, compound

HRID 402028Notes

Reaction equation

HRID 402028 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[C:19]([O:21][CH:22]3[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]3)[N:18]=[N:17][C:16]=2[CH2:29][CH2:30][CH2:31][CH3:32])=[CH:11][C:10]=1[O:33][CH3:34])C1C=CC=CC=1>CO.C(OCC)(=O)C.[Pd]>[CH2:29]([C:16]1[N:17]=[N:18][C:19]([O:21][CH:22]2[CH2:23][CH2:24][N:25]([CH3:28])[CH2:26][CH2:27]2)=[CH:20][C:15]=1[C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([O:33][CH3:34])[CH:11]=1)[CH2:30][CH2:31][CH3:32]

Participants

4

Reactant 1

HCID 67373515HCID 67373515, compound

Product 1

HCID 136386260HCID 136386260, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

To a solution of 4-(4-benzyloxy-3-methoxy-phenyl)-3-butyl-6-(1-methyl-piperidin-4-yloxy)-pyridazine (1.0 mmol, 462 mg) in methanol/ethyl acetate (10 mL, 1/1) was added 10% palladium on activated carbon (70 mg). The mixture was repeatedly de-gassed under vacuum, filled with hydrogen for 3 times. Then hydrogen balloons were attached to the reaction, which was stirred at room temperature for 2 hours. TLC/LCMS monitored to completion. The mixture was then filtered through celite, the celite cake was washed with 1/1 methanol/ethyl acetate for 3 times, and the organic layers were combined and condensed under reduced pressure to give 4-[3-butyl-6-(1-methyl-piperidin-4-yloxy)-pyridazin-4-yl]-2-methoxy-phenol as a white powder (327 mg), which was used directly in the next step.

Workup

  1. customThe mixture was repeatedly de-gassed under vacuum
  2. additionfilled with hydrogen for 3 times
  3. customThen hydrogen balloons were attached to the reaction, which
  4. filtrationThe mixture was then filtered through celite
  5. washthe celite cake was washed with 1/1 methanol/ethyl acetate for 3 times
  6. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-ff278ff80718495f8e6280f92fb41115
Source dataset
uspto-grants-2014_06
Patent number
US08741900B2

Reaction notes

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