Potassium Carbonate → 2-[4-(Benzyloxy)phenyl]-6-(cyclopropylmethoxy)[1,2,4]triazolo[1,5-a]pyridine

HRID 1026322노트

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HRID 1026322 반응식
[NH2:1]OS(=O)(=O)O.C(=O)([O-])O.[Na+].[CH:12]1([CH2:15][O:16][C:17]2[CH:18]=[CH:19][C:20]([NH2:23])=[N:21][CH:22]=2)[CH2:14][CH2:13]1.[CH2:24]([O:31][C:32]1[CH:39]=[CH:38][C:35]([CH:36]=O)=[CH:34][CH:33]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>O.C(O)C>[CH2:24]([O:31][C:32]1[CH:39]=[CH:38][C:35]([C:36]2[N:23]=[C:20]3[CH:19]=[CH:18][C:17]([O:16][CH2:15][CH:12]4[CH2:13][CH2:14]4)=[CH:22][N:21]3[N:1]=2)=[CH:34][CH:33]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

참가 물질

8

반응물 5

HCID 11430Potassium CarbonateHCID 76284hydroxylamine-O-sulfonic acidHCID 78109Benzaldehyde, 4-(phenylmethoxy)-HCID 516892Sodium BicarbonateHCID 284136605-(Cyclopropylmethoxy)pyridin-2-amine

생성물 1

HCID 677783102-[4-(Benzyloxy)phenyl]-6-(cyclopropylmethoxy)[1,2,4]triazolo[1,5-a]pyridine수율 3.6%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

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온도
70 °C

실험 절차

(Aminooxy)(hydroxy)sulfane dioxide (3.39 g) was dissolved in water (10 mL), and saturated aqueous sodium hydrogen carbonate solution was added dropwise thereto at 0° C. to neutralize the solution. To the obtained mixture was added a solution of 5-(cyclopropylmethoxy)pyridin-2-amine (1.64 g) in ethanol (25 ml) at 0° C., and the mixture was stirred at 70° C. for 3 days. To the reaction mixture were added 4-(benzyloxy)benzaldehyde (2.12 g) and potassium carbonate (4.15 g), and the mixture was stirred at 70° C. for 2 hr. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with ethyl acetate and water, and the aqueous layer was separated from the organic layer. The separated aqueous layer was extracted again with ethyl acetate. The combined organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound as a yellow solid (134 mg).

후처리

  1. customat 0° C.
  2. stirringthe mixture was stirred at 70° C. for 2 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionthe residue was diluted with ethyl acetate and water
  5. customthe aqueous layer was separated from the organic layer
  6. extractionThe separated aqueous layer was extracted again with ethyl acetate
  7. washThe combined organic layer was washed with saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-1a207f86d7944624a067fc5a8c49968a
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08729102B2

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