Trifluoroacetic acid → Ethyl 7-amino-[1,2,4]triazolo[1,5-a]pyridine-2-carboxylate

HRID 1802192Notes

Reaction equation

HRID 1802192 reaction equation
C(OC([NH:8][C:9]1[CH:14]=[CH:13][N:12]2[N:15]=[C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:17]=[C:11]2[CH:10]=1)=O)(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[NH2:8][C:9]1[CH:14]=[CH:13][N:12]2[N:15]=[C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:17]=[C:11]2[CH:10]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 67776374Ethyl 7-(tert-butoxycarbonylamino)-[1,2,4]triazolo[1,5-a]pyridine-2-carboxylate

Product 1

HCID 67776028Ethyl 7-amino-[1,2,4]triazolo[1,5-a]pyridine-2-carboxylateYield 75.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl 7-(tert-butoxycarbonylamino)-[1,2,4]triazolo[1,5-a]pyridine-2-carboxylate (1.07 g, 3.49 mmol) in dichloromethane (5 ml) and trifluoroacetic acid (5.38 ml, 69.9 mmol) is stirred for 3 hours at 25° C. The mixture is made basic using sat. aqueous sodium carbonate solution and extracted with ethyl acetate. The organic layer is washed with water and brine, dried with magnesium sulfate and the solvent is removed in vacuo affording ethyl 7-amino-[1,2,4]triazolo[1,5-a]pyridine-2-carboxylate (543 mg, 75.4%) as a light yellow solid. mp.: 150-171° C. MS: m/z=207.0 (M+H+).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer is washed with water and brine
  3. dry with materialdried with magnesium sulfate
  4. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-3c1e7be098a344778e02283a53e96578
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

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