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

HRID 1802192Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1802192
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

Komponenten

5

Edukt 3

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

Produkt 1

HCID 67776028Ethyl 7-amino-[1,2,4]triazolo[1,5-a]pyridine-2-carboxylateAusbeute 75,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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+).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-3c1e7be098a344778e02283a53e96578
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08349824B2

Notizen zur Reaktion

Wird geladen…