Hydrochloric Acid → HCID 15292079, compound

HRID 2396753Notes

Reaction equation

HRID 2396753 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8](CC2C=CC=CC=2)CC2C=CC=CC=2)[C:5]2[N:23]=[C:24]([CH3:31])[N:25]([CH2:26][CH2:27][O:28][CH2:29][CH3:30])[C:4]=2[C:3]=1[CH3:32].Cl>CO.[OH-].[OH-].[Pd+2]>[CH2:29]([O:28][CH2:27][CH2:26][N:25]1[C:4]2[C:3]([CH3:32])=[CH:2][N:7]=[C:6]([NH2:8])[C:5]=2[N:23]=[C:24]1[CH3:31])[CH3:30]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 15292078HCID 15292078, compound

Product 1

HCID 15292079HCID 15292079, compoundYield 49.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

6-Chloro-1-(2-ethoxyethyl)-2,7-dimethyl-N4,N4 -bis(phenylmethyl)-1H-imidazo[4,5-c]pyridin-4-amine (0.7 g, 1.56 mmole) was taken up in methanol saturated with anhydrous hydrochloric acid (100 mL), combined with palladium hydroxide on carbon and then hydrogenated on a Paar apparatus for four hours. The reaction mixture was filtered to remove the catalyst then concentrated under vacuum. The residue was partitioned between methylene chloride/water/sodium bicarbonate. The methylene chloride layer was separated, dried over magnesium sulfate then concentrated under vacuum to provide an off white solid. This material was recrystallized from ethyl acetate/hexane to provide 0.18 g of the desired product as a solid, m.p. 129°-130° C. Analysis: Calculated for: C12H18N4O+1/4H2O: % C, 60.35; % H, 7.81; % N, 23.46; Found: % C, 60.64; % H, 7.50; % N, 23.39.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the catalyst
  3. concentrationthen concentrated under vacuum
  4. customThe residue was partitioned between methylene chloride/water/sodium bicarbonate
  5. customThe methylene chloride layer was separated
  6. dry with materialdried over magnesium sulfate
  7. concentrationthen concentrated under vacuum
  8. customto provide an off white solid
  9. customThis material was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-d99e5790dfac4e149cec4fbac9e1c791
Source dataset
uspto-grants-1996_02
Patent number
US05494916

Reaction notes

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