HCID 86640028, compound → 4-(5-Methyl-1,3,4-oxadiazol-2-yl)pyridin-2-amine

HRID 452625Notes

Reaction equation

HRID 452625 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([C:14]2[O:15][C:16]([CH3:19])=[N:17][N:18]=2)[CH:11]=[CH:10][N:9]=1)(C)(C)C>FC(F)(F)C(O)=O>[CH3:19][C:16]1[O:15][C:14]([C:12]2[CH:11]=[CH:10][N:9]=[C:8]([NH2:7])[CH:13]=2)=[N:18][N:17]=1

Participants

3

Reactant 1

HCID 86640028HCID 86640028, compound

Product 1

HCID 686630234-(5-Methyl-1,3,4-oxadiazol-2-yl)pyridin-2-amineYield 92%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of tert-butyl[4-(5-methyl-1,3,4-oxadiazol-2-yl)pyridin-2-yl]carbamate (440 mg, 1.59 mmol) and trifluoroacetic acid (10 mL) was stirred at room temperature for 1.5 hr. The reaction mixture was concentrated under reduced pressure, and the residue was neutralized with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate/tetrahydrofuran. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give the title compound (257 mg, yield 92%) as pale-yellow crystals.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionextracted with ethyl acetate/tetrahydrofuran
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a68e55e8e25c46db99f0ec70c13cfffc
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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