HCID 18174630, compound → HCID 18174664, compound

HRID 395752Notes

Reaction equation

HRID 395752 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([NH:15][C:16](=[O:36])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[NH:23][C:24](=[O:35])[C:25]2[CH:30]=[CH:29][C:28]([C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:27][CH:26]=2)[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1.[H][H]>O1CCCC1.[Pd]>[C:31]([C:28]1[CH:29]=[CH:30][C:25]([C:24]([NH:23][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[C:16]([NH:15][C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([OH:8])[CH:10]=2)=[O:36])=[O:35])=[CH:26][CH:27]=1)([CH3:34])([CH3:32])[CH3:33]

Participants

5

Reactant 2

HCID 18174630HCID 18174630, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18174664HCID 18174664, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of N-(3-benzyloxyphenyl)-2-[(4-tert-butylbenzoyl)amino]benzamide (0.58 g, 1.2 mmol) in tetrahydrofuran (50 mL) was added 10% palladium-on-carbon (0.29 g). The vessel was placed under vacuum and the atmosphere was replaced with hydrogen (1 atm). After 12 h, the balloon was removed and the mixture was filtered through diatomaceous earth and concentrated in vacuo. The residue was dissolved in ethyl acetate and washed with saturated aqueous sodium chloride solution, dried (magnesium sulfate), filtered, and concentrated In vacuo to give 0.41 g (88%) of the title compound as an off-white solid.

Workup

  1. customthe balloon was removed
  2. filtrationthe mixture was filtered through diatomaceous earth
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with saturated aqueous sodium chloride solution
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated In vacuo

Sources & evidence

ORD record
ord-adbf83659d0b4e51bbcf64e68600ca51
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Reaction notes

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