HCID 57479901, compound → HCID 57479903, compound

HRID 11484Notes

Reaction equation

HRID 11484 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 36.1%

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 under hydrogen at 1 atm and room temperature 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 0.58 g (36%) of the titled compound 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-5e6ea597a9fd4f3e9d2e415a9a3753ea
Source dataset
uspto-grants-2006_08
Patent number
US07098226B2

Reaction notes

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