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

HRID 71183

반응식

HRID 71183 반응식
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[N:29]=[C:28]([C:30]([NH:32][NH2:33])=O)[CH:27]=[CH:26][C:25]=1[N:34]1[CH:38]=[C:37]([CH3:39])[N:36]=[CH:35]1>C(#N)C>[CH3:22][O:23][C:24]1[N:29]=[C:28]([C:30]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:33][N:32]=2)[CH:27]=[CH:26][C:25]=1[N:34]1[CH:38]=[C:37]([CH3:39])[N:36]=[CH:35]1

참가 물질

5

반응물 3

HCID 977733-Carbethoxy-2-piperidoneHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 666083826-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridine-2-carbohydrazide

생성물 1

HCID 66607844ethyl 3-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate수율 40.1%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a mixture of ethyl 2-oxopiperidine-3-carboxylate (3.5 g) in acetonitrile (100 mL) was added trimethyloxonium tetrafluoroborate (3.0 g) at room temperature, and the mixture was stirred at room temperature for 2 hr. 6-Methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridine-2-carbohydrazide (5.0 g) was added to the reaction mixture at room temperature, and the solvent was evaporated under reduced pressure. Methanol (100 mL) was added to the residue at room temperature, and the mixture was stirred for 2 hr under reflux. The solvent in the reaction mixture was evaporated under reduced pressure, acetonitrile (100 mL) was added to the residue at room temperature, and the mixture was stirred at 80° C. overnight. The solvent in the reaction mixture was evaporated under reduced pressure, the residue was 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 of another lot synthesized similarly was combined, and the mixture was purified by silica gel column chromatography (methanol/ethyl acetate) to give the title compound (3.1 g).

후처리

  1. customthe solvent was evaporated under reduced pressure
  2. additionMethanol (100 mL) was added to the residue at room temperature
  3. stirringthe mixture was stirred for 2 hr
  4. temperatureunder reflux
  5. customThe solvent in the reaction mixture was evaporated under reduced pressure, acetonitrile (100 mL)
  6. additionwas added to the residue at room temperature
  7. stirringthe mixture was stirred at 80° C. overnight
  8. customThe solvent in the reaction mixture was evaporated under reduced pressure
  9. additionthe residue was diluted with ethyl acetate and saturated aqueous sodium hydrogen carbonate solution
  10. washthe mixture was washed with saturated brine
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customthe solvent was evaporated under reduced pressure
  13. customThe residue of another lot synthesized similarly
  14. customthe mixture was purified by silica gel column chromatography (methanol/ethyl acetate)

출처 및 근거

ORD 기록
ord-4cf9fdc16a2e4e439ba3b09fe645dcf0
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822699B2

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