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

HRID 71117

반응식

HRID 71117 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[CH:25]=[C:26]([CH:31]=[CH:32][C:33]=1[C:34]1[O:38][C:37]([CH3:39])=[N:36][CH:35]=1)[C:27]([NH:29][NH2:30])=O>C(#N)C>[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[C:34]1[O: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 666079613-Methoxy-4-(2-methyloxazol-5-yl)benzohydrazide

생성물 1

HCID 66608236Ethyl 3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate수율 37.5%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of ethyl 2-oxo-3-piperidinecarboxylate (34.6 g), trimethyloxonium tetrafluoroborate (95%, 31.5 g) and acetonitrile (600 mL) was stirred at room temperature for 16 hr. 3-Methoxy-4-(2-methyl-1,3-oxazol-5-yl)benzohydrazide (50.0 g) was added to the reaction mixture at room temperature, and the mixture was heated under reflux for 24 hr, allowed to cool to room temperature and concentrated under reduced pressure. Saturated aqueous sodium hydrogen carbonate solution was added to the residue, the insoluble material was filtered off through celite, and the filtrate was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was crystallized from methanol/ethyl acetate to give the title compound (29.0 g).

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 24 hr
  3. temperatureto cool to room temperature
  4. concentrationconcentrated under reduced pressure
  5. additionSaturated aqueous sodium hydrogen carbonate solution was added to the residue
  6. filtrationthe insoluble material was filtered off through celite
  7. extractionthe filtrate was extracted with ethyl acetate
  8. washThe extract was washed with saturated brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. customthe solvent was evaporated under reduced pressure
  11. customThe residue was crystallized from methanol/ethyl acetate

출처 및 근거

ORD 기록
ord-224e5386694944ffa09baf768ee21b84
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822699B2

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