Hydrochloric Acid → HCID 15292079, compound

HRID 1757583Notes

Reaction equation

HRID 1757583 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.C(OCC)(=O)C.CCCCCC>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

6

Reactant 3

HCID 313Hydrochloric AcidHCID 15292078HCID 15292078, compoundHCID 21226206Ethyl acetate hexane

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 wasrecrystallized 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

Sources & evidence

ORD record
ord-8f90903c39344eebae3df40187f34327
Source dataset
uspto-grants-1995_08
Patent number
US05446153

Reaction notes

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