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 71166

反応式

HRID 71166 の反応式
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

参加物

7

反応物 3

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

生成物 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-carboxylate収率 38.2%

試薬・触媒・溶媒 3

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-6a3e7fab210146a481e15b7772ff17ba
出典データセット
uspto-grants-2014_09
特許番号
US08822699B2

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