Reaction #1563937

ord-7bfb50603096482e866bdd3591b6f27f

Reaction equation

CCOC(=O)c1cnn2ccc(NC(=O)OC(C)(C)C)c(F)c12
ethyl 5-((tert-butoxycarbonyl)amino)-4-fluoropyrazolo[1,5-a]pyridine-3-carboxylate
O=C(O)C(F)(F)F
TFA
CCOC(=O)c1cnn2ccc([NH3+])c(F)c12.O=C([O-])C(F)(F)F
title compound
Yield 98.8%
CCOC(=O)c1cnn2ccc([NH3+])c(F)c12.O=C([O-])C(F)(F)F
3-(ethoxycarbonyl)-4-fluoropyrazolo[1,5-a]pyridin-5-aminium 2,2,2-trifluoroacetate
Yield 98.8%

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherreaction mass
  2. 2
    Concentrationwas concentrated at temperature below 40° C. under reduced pressure

Procedure

To a solution of ethyl 5-((tert-butoxycarbonyl)amino)-4-fluoropyrazolo[1,5-a]pyridine-3-carboxylate (7 g, 21 mmol) in DCM (60 mL), TFA (12 g, 108 mmol) was added at 0-5° C. drop wise over a period of 30 min, then stirred at room temperature for 2 hrs, reaction mass was concentrated at temperature below 40° C. under reduced pressure to afford the title compound (7 g) which was used in the next step without further purification, MS m/z 223.2 (M+)

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09402833B2uspto-grants-2016_08