HCID 57479901, compound → HCID 57479903, compound

HRID 18413Notes

Reaction equation

HRID 18413 reaction equation
[C:1]12([CH2:11][CH2:12][N:13]([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[C:14](=[O:25])[CH2:15][CH2:16][N:17]=[CH:18][C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2>CO.[Pd]>[C:1]12([CH2:11][CH2:12][N:13]([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[C:14](=[O:25])[CH2:15][CH2:16][NH:17][CH2:18][C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

Participants

4

Reactant 1

HCID 57479901HCID 57479901, compound

Product 1

HCID 57479903HCID 57479903, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3-(4-Pyridylmethylideneamino)propionic acid N-[2-(1-adamantyl)ethyl]-N-pentylamide (Compound No. 21-1, 1.6 g, 3.9 mmol) was dissolved in methanol, 10% palladium on carbon (catalytic amount) was added to the solution, and the mixture was stirred at room temperature under hydrogen at 1 atm for seven hours. The 10% palladium on carbon was filtered out, the filtrate was concentrated under reduced pressure, and the concentrate was purified by silica gel column chromatography to give the target compound (0.58 g, 36%) as an oily matter.

Workup

  1. filtrationThe 10% palladium on carbon was filtered out
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customthe concentrate was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ba3aa8bec80941fdb6a21249b7021f3a
Source dataset
uspto-grants-2010_06
Patent number
US07741346B2

Reaction notes

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