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

HRID 1026322ノート

反応式

HRID 1026322 の反応式
[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

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
70 °C

実験手順

(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).

後処理

  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)

出典と根拠

ORDレコード
ord-1a207f86d7944624a067fc5a8c49968a
出典データセット
uspto-grants-2014_05
特許番号
US08729102B2

反応ノート

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