HCID 67759517, compound → HCID 15231842, compound

HRID 1779701Notes

Reaction equation

HRID 1779701 reaction equation
C1(C[N:8](CC2C=CC=CC=2)[C:9]2[C:18]3[N:19]=[C:20]([CH2:26][CH:27]([CH3:29])[CH3:28])[N:21]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:17]=3[C:16]3[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=3[N:10]=2)C=CC=CC=1>[OH-].[OH-].[Pd+2].C(O)=O>[CH3:24][CH:23]([CH3:25])[CH2:22][N:21]1[C:17]2[C:16]3[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=3[N:10]=[C:9]([NH2:8])[C:18]=2[N:19]=[C:20]1[CH2:26][CH:27]([CH3:29])[CH3:28]

Participants

4

Reactant 1

HCID 67759517HCID 67759517, compound

Product 1

HCID 15231842HCID 15231842, compoundYield 65.6%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 284Formic AcidSolvent

Procedure

N,N-Bis(phenylmethyl)-6,7,8,9-tetrahydro-1,2-di(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine (1.61 g, 3.3 mmole), palladium hydroxide on carbon (0.50 g, Pearlman's catalyst) and formic acid (10 mL) were combined and heated at reflux for 20 hours. The reaction mixture was cooled to ambient temperature, filtered through a layer of celite and diluted with water (about 20 mL). The resulting mixture was cooled to 0° C., made basic by the addition of 28% ammonium hydroxide then extracted with methylene chloride (3×50 mL). The extracts were combined, dried over magnesium sulfate and concentrated to provide a white solid. The solid was purified by silica gel chromatography eluting with methylene chloride:methanol 90:10 to provide 0.65 g of the desired product as a white solid, m.p.160°-161° C. Analysis: Calculated for C18H28N4 : %C, 71.96; %H, 9.39; %N, 18.65; Found: %C, 71.66; %H, 9.37; %N, 18.46.

Workup

  1. temperatureheated
  2. temperatureat reflux for 20 hours
  3. filtrationfiltered through a layer of celite and
  4. additiondiluted with water (about 20 mL)
  5. temperatureThe resulting mixture was cooled to 0° C.
  6. additionmade basic by the addition of 28% ammonium hydroxide
  7. extractionthen extracted with methylene chloride (3×50 mL)
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated
  10. customto provide a white solid
  11. customThe solid was purified by silica gel chromatography
  12. washeluting with methylene chloride:methanol 90:10

Sources & evidence

ORD record
ord-85826615e2dd47c78f84399ee33a84fe
Source dataset
uspto-grants-1997_05
Patent number
US05627281

Reaction notes

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