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

HRID 1026322Notes

Reaction equation

HRID 1026322 reaction equation
[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

Participants

8

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

(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).

Workup

  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)

Sources & evidence

ORD record
ord-1a207f86d7944624a067fc5a8c49968a
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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