Water → HCID 178459396, compound

HRID 1688606Notes

Reaction equation

HRID 1688606 reaction equation
[NH:1]1[CH:5]=[N:4][C:3]([NH2:6])=[N:2]1.O=[C:8]1[CH2:11][CH:10]([C:12]([O:14][CH2:15][CH2:16][CH3:17])=[O:13])[CH2:9]1.C([BH3-])#N.[Na+].O>C(O)(=O)C>[N:1]1[N:2]=[C:3]([NH:6][CH:8]2[CH2:11][CH:10]([C:12]([O:14][CH2:15][CH2:16][CH3:17])=[O:13])[CH2:9]2)[NH:4][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 67008885Propyl 3-oxocyclobutanecarboxylateHCID 178418311HCID 178418311, compound

Product 1

HCID 178459396HCID 178459396, compoundYield 49.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution (100 mL) of 1H-1,2,4-triazol-3-amine (6.7 g) and propyl 3-oxocyclobutanecarboxylate (14 g) in acetic acid was added sodium cyanoborohydride (14 g), and the mixture was stirred at room temperature for 16 hr. Water was added to the reaction mixture, and the solvent was evaporated under reduced pressure. The obtained residue was poured into saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with a mixed solvent of ethyl acetate and isopropyl alcohol (3:1). The obtained extract was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound as a colorless solid (8.8 g, 49%).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. additionThe obtained residue was poured into saturated aqueous sodium hydrogen carbonate
  3. extractionthe mixture was extracted with a mixed solvent of ethyl acetate and isopropyl alcohol (3:1)
  4. extractionThe obtained extract
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-99cd196cdcdd4bcdbe3955655f9f31b1
Source dataset
uspto-grants-2012_04
Patent number
US08148383B2

Reaction notes

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