Triethylamine → HCID 178497018, compound

HRID 2391736Notes

Reaction equation

HRID 2391736 reaction equation
Cl.Cl.[NH:3]1[C:11]2[CH2:10][C@@H:9]([C:12]([O:14][CH3:15])=[O:13])[NH:8][CH2:7][C:6]=2[N:5]=[CH:4]1.C(N(CC)CC)C.[Se](=O)=O>O1CCOCC1>[NH:3]1[C:11]2[CH:10]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[N:8]=[CH:7][C:6]=2[N:5]=[CH:4]1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 24007Selenium DioxideHCID 178501029HCID 178501029, compound

Product 1

HCID 178497018HCID 178497018, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

68.5 g methyl (6S)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylate dihydrochloride, 81.8 g triethylamine and 63.3 g selenium dioxide were suspended in 1.1 l anhydrous 1,4-dioxane. The mixture was refluxed for 2 h. 26.3 g triethylamine were added and the mixture was allowed to cool down to room temperature and stirred overnight. The solvent was removed under reduced pressure and the residue was suspended in 300 ml methanol. 46.8 g triethylamine were added to adjust to pH 8-9. The resulting precipitate was filtered and washed with 70 ml methanol. The precipitate was treated with 500 ml N,N-dimethylformamide, stirred at 140° C. for 30 minutes and filtered hot. Upon cooling to room temperature, precipitation takes place. The precipitate was filtered, washed with 80 ml cold methanol and dried under vacuum to yield the title compound.

Workup

  1. temperatureThe mixture was refluxed for 2 h
  2. customThe solvent was removed under reduced pressure
  3. addition46.8 g triethylamine were added
  4. filtrationThe resulting precipitate was filtered
  5. washwashed with 70 ml methanol
  6. additionThe precipitate was treated with 500 ml N,N-dimethylformamide
  7. stirringstirred at 140° C. for 30 minutes
  8. filtrationfiltered hot
  9. temperatureUpon cooling to room temperature
  10. customprecipitation
  11. filtrationThe precipitate was filtered
  12. washwashed with 80 ml cold methanol
  13. customdried under vacuum

Sources & evidence

ORD record
ord-26b4428ef2ba4ff7ba87d8592ab419e1
Source dataset
uspto-grants-2012_09
Patent number
US08273890B2

Reaction notes

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