3-Carbethoxy-2-piperidone → ethyl 3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate

HRID 1398194Notes

Reaction equation

HRID 1398194 reaction equation
O=[C:2]1[CH:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6][CH2:5][CH2:4][NH:3]1.F[B-](F)(F)F.C[O+](C)C.[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH:31]=[CH:32][C:33]=1[N:34]1[CH:38]=[C:37]([CH3:39])[N:36]=[CH:35]1)[C:27]([NH:29][NH2:30])=O>C(#N)C.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>[CH3:22][O:23][C:24]1[CH:25]=[C:26]([C:27]2[N:3]3[CH2:4][CH2:5][CH2:6][CH:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:2]3=[N:30][N:29]=2)[CH:31]=[CH:32][C:33]=1[N:34]1[CH:38]=[C:37]([CH3:39])[N:36]=[CH:35]1

Participants

7

Reactant 3

HCID 977733-Carbethoxy-2-piperidoneHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 666078503-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzohydrazide

Product 1

HCID 66608063ethyl 3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylateYield 38.2%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a mixture of ethyl 2-oxopiperidine-3-carboxylate (1.86 g) in acetonitrile (20 mL) was added trimethyloxonium tetrafluoroborate (1.61 g) at room temperature, and the mixture was stirred at room temperature for 2 hr. 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzohydrazide (2.23 g) was added to the reaction mixture at room temperature, and the mixture was heated under reflux for 2 hr. The reaction mixture was allowed to cool to room temperature, and diluted with ethyl acetate and saturated aqueous sodium hydrogen carbonate solution, the mixture was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was collected by filtration, and washed with ethyl acetate to give the title compound (1.32 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hr
  3. temperatureto cool to room temperature
  4. washthe mixture was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. filtrationThe residue was collected by filtration
  8. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-700de8ee69274cd49917c158e7af74bf
Source dataset
uspto-grants-2014_12
Patent number
US08901309B2

Reaction notes

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