Water → HCID 19038972, compound

HRID 263727Notes

Reaction equation

HRID 263727 reaction equation
[CH3:1][C:2]1[N:3]([CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:4]2[CH:9]=[C:8]([CH3:10])[N:7]=[C:6]([N:11](CC3C=CC=CC=3)CC3C=CC=CC=3)[C:5]=2[N:26]=1.C(=O)(O)[O-].[Na+].O>C(O)=O.CO.[OH-].[OH-].[Pd+2]>[CH3:1][C:2]1[N:3]([CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:4]2[CH:9]=[C:8]([CH3:10])[N:7]=[C:6]([NH2:11])[C:5]=2[N:26]=1

Participants

7

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 15292066HCID 15292066, compound

Product 1

HCID 19038972HCID 19038972, compoundYield 87.5%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 284Formic AcidSolventHCID 887MethanolSolvent

Procedure

Palladium hydroxide on carbon (0.5 g, Pearlman's catalyst) was added to a mixture of 2,6-dimethyl-1-(2-phenylethyl)-N4,N4 -bis(phenylmethyl)-1H-imidazo[4,5-c]pyridin-4-amine (2.3 g, 5.15 mmole) in formic acid (10 mL). The reaction mixture was heated at reflux overnight. An additional 0.5 g of catalyst was added and refluxing was continued overnight. The reaction mixture was neutralized with saturated sodium bicarbonate solution, diluted with methanol then filtered through a layer of celite to remove the catalyst. The celite layer was flushed with methylene chloride and methanol. The filtrates were combined and concentrated under vacuum to provide a mixture of water and a solid. This mixture was extracted with methylene chloride. The extract was washed with water, dried over magnesium sulfate and concentrated under vacuum to provide 1.2 g of a tan solid. This solid was recrystallized from ethanol to provide 0.24 g of the desired product as a solid, m.p. 185°-187° C. Analysis: Calculated for C16H18N4 : % C, 72.15; % H, 6.81; % N, 21.04; Found: % C, 71.51; % H, 6.88; % N, 20.61.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. temperaturerefluxing
  4. filtrationthen filtered through a layer of celite
  5. customto remove the catalyst
  6. customThe celite layer was flushed with methylene chloride and methanol
  7. concentrationconcentrated under vacuum
  8. customto provide
  9. extractionThis mixture was extracted with methylene chloride
  10. washThe extract was washed with water
  11. dry with materialdried over magnesium sulfate
  12. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-6f4b8420c5164ffebdc920a5344b13ec
Source dataset
uspto-grants-1997_07
Patent number
US05644063

Reaction notes

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