Trifluoroacetic acid → 6-Fluoro-3-(R)-pyrrolidin-3-yl-[1,2,4]triazolo[4,3-a]pyridine

HRID 1402296Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1402296
C(OC([N:8]1[CH2:12][CH2:11][C@@H:10]([C:13]2[N:17]3[CH:18]=[C:19]([F:22])[CH:20]=[CH:21][C:16]3=[N:15][N:14]=2)[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:22][C:19]1[CH:20]=[CH:21][C:16]2[N:17]([C:13]([C@@H:10]3[CH2:11][CH2:12][NH:8][CH2:9]3)=[N:14][N:15]=2)[CH:18]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 86687137(R)-3-(6-Fluoro-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 866871396-Fluoro-3-(R)-pyrrolidin-3-yl-[1,2,4]triazolo[4,3-a]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of Intermediate 90b (335 mg, 1.09 mmol) and TFA (0.812 mL, 10.9 mmol) in DCM (5 mL) was stirred at reflux for 45 min. The cooled solution was concentrated in vacuo, redissolved in MeOH (2 mL), applied to an SCX-2 cartridge (10 g) and washed with MeOH (50 mL). The product was eluted with 2M NH3 in MeOH; concentration in vacuo left the title compound as a pale yellow solid (225 mg, >99%). LCMS (Method 3): Rt 0.44 min, m/z 207 [MH+].

Aufarbeitung

  1. temperatureat reflux for 45 min
  2. concentrationThe cooled solution was concentrated in vacuo
  3. dissolutionredissolved in MeOH (2 mL)
  4. washwashed with MeOH (50 mL)
  5. washThe product was eluted with 2M NH3 in MeOH
  6. concentrationconcentration in vacuo
  7. waitleft the title compound as a pale yellow solid (225 mg, >99%)

Quellen und Nachweise

ORD-Eintrag
ord-a622b22dfa404f6992534e625711f53b
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08907094B2

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