Triethylamine → HCID 21094309, compound

HRID 1350087Notes

Reaction equation

HRID 1350087 reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH2:10][NH:9][CH2:8][CH:7]2[CH2:14][CH2:15][NH:16][C:17](=[O:20])[CH2:18][CH3:19].C(N(CC)CC)C>CO.C1(C)C=CC=CC=1.[Pd]>[ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[N:9][CH:8]=[C:7]2[CH2:14][CH2:15][NH:16][C:17](=[O:20])[CH2:18][CH3:19]

Participants

6

Reactant 2

HCID 8471TriethylamineHCID 21094301HCID 21094301, compound

Product 1

HCID 21094309HCID 21094309, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

The compound of Example 5 is dissolved in a minimum of methanol with the application of heat and then diluted with toluene. 1.5 equivalents of triethylamine are then added to the solution, and the reaction mixture is subsequently heated at reflux in the presence of palladium-on-carbon (10% by weight) for 3 hours. After removal of the catalyst by filtration, the solution is evaporated under reduced pressure. The oil obtained is purified by chromatography on silica gel (eluant dichlormethane/methanol 9/1). The purified oil is taken up in ether saturated with HCl(g) and stirred until a precipitate is obtained. The precipitate so formed is suction-filtered off and placed under vacuum in a dessicator. The title product is obtained in the form of a white solid.

Workup

  1. temperatureof heat
  2. temperaturethe reaction mixture is subsequently heated
  3. customAfter removal of the catalyst
  4. filtrationby filtration
  5. customthe solution is evaporated under reduced pressure
  6. customThe oil obtained
  7. customis purified by chromatography on silica gel (eluant dichlormethane/methanol 9/1)
  8. customis obtained
  9. customThe precipitate so formed
  10. filtrationis suction-filtered off

Sources & evidence

ORD record
ord-70c087362542495dad0b48d0c75786dc
Source dataset
uspto-grants-2007_05
Patent number
US07214689B2

Reaction notes

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