Acetophenone → HCID 58835269, compound

HRID 1992598Notes

Reaction equation

HRID 1992598 reaction equation
[NH2:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[C:14]2[C:13]([CH3:15])=[C:12]([CH3:16])[N:11]=[C:10]([NH2:17])[C:9]=2[N:8]=[C:7]1[CH2:18][CH2:19][CH3:20].[C:21]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=O)[CH3:22].Cl.N1C=CC=CC=1>CO>[NH2:17][C:10]1[C:9]2[N:8]=[C:7]([CH2:18][CH2:19][CH3:20])[N:6]([CH2:5][CH2:4][CH2:3][O:2]/[N:1]=[C:21](/[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)\[CH3:22])[C:14]=2[C:13]([CH3:15])=[C:12]([CH3:16])[N:11]=1

Participants

5

Reactant 3

HCID 7410AcetophenoneHCID 10176127Pyridinium chloride2×HCID 68539547HCID 68539547, compound

Product 1

HCID 58835269HCID 58835269, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 1-[3-(aminooxy)propyl]-6,7-dimethyl-2-propyl-1H-imidazo[4,5-c]pyridin-4-amine (0.64 g, 2.3 mmol) and acetophenone (325 μL, 2.76 mmol) in methanol (23 mL) was stirred overnight at room temperature, then heated at 50° C. for 4 hours. Pyridine hydrochloride (100 mg) was added to the solution and stirring was continued at 50° C. overnight. Additional pyridine hydrochloride was added and the solution was heated at reflux for 5 hours. The solvent was removed under reduced pressure and the resulting off-white solid was partitioned between chloroform (100 mL) and saturated aqueous sodium carbonate (30 mL). The aqueous layer was extracted with chloroform (3×30 mL). The combined organic layers were washed with saturated aqueous sodium carbonate (2×20 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by chromatography on a HORIZON HPFC system (silica gel, gradient elution with 5-30% CMA in chloroform) to yield a solid that was triturated with acetonitrile and dried under vacuum at 70° C. overnight to provide 105 mg of (1E)-1-phenylethanone O-[3-(4-amino-6,7-dimethyl-2-propyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]oxime as a white powder, mp 125.0-127.0° C. Anal. Calcd for C22H29N5O: C, 69.63; H, 7.70; N, 18.45. Found: C, 69.41; H, 7.73; N, 18.36.

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux for 5 hours
  3. customThe solvent was removed under reduced pressure
  4. customthe resulting off-white solid was partitioned between chloroform (100 mL) and saturated aqueous sodium carbonate (30 mL)
  5. extractionThe aqueous layer was extracted with chloroform (3×30 mL)
  6. washThe combined organic layers were washed with saturated aqueous sodium carbonate (2×20 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe crude product was purified by chromatography on a HORIZON HPFC system (silica gel, gradient elution with 5-30% CMA in chloroform)
  11. customto yield a solid
  12. customthat was triturated with acetonitrile
  13. customdried under vacuum at 70° C. overnight

Sources & evidence

ORD record
ord-980da5d825034564a3f1485a6424e896
Source dataset
uspto-grants-2010_01
Patent number
US07648997B2

Reaction notes

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