Reaction #70344

ord-173a0ffe83b349cd963070606fb7fc29

Reaction equation

Cc1ccc(Nc2ccc(N3CCOCC3)nc2)c(C(=O)OC(C)(C)C)c1
5-methyl-2-(6-morpholinopyridin-3-ylamino)benzoate tert-butyl ester
O=C(O)C(F)(F)F
TFA
→
Cc1ccc(Nc2ccc(N3CCOCC3)nc2)c(C(=O)O)c1
expected product
Cc1ccc(Nc2ccc(N3CCOCC3)nc2)c(C(=O)O)c1
5-Methyl-2-(6-morpholinopyridin-3-ylamino)benzoic acid

Reactants

Cc1ccc(Nc2ccc(N3CCOCC3)nc2)c(C(=O)OC(C)(C)C)c1
5-methyl-2-(6-morpholinopyridin-3-ylamino)benzoate tert-butyl ester
O=C(O)C(F)(F)F
TFA

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherThe solvent was evaporated
  2. 2
    Otherthe residue was triturated in diethyl ether
  3. 3
    OtherThe solid formed
  4. 4
    Filtrationwas filtered off
  5. 5
    Otherto afford

Procedure

A solution of 5-methyl-2-(6-morpholinopyridin-3-ylamino)benzoate tert-butyl ester in TFA (0.6 ml, 7.58 mmol) was stirred at room temperature for 1 hour. The solvent was evaporated and the residue was triturated in diethyl ether. The solid formed was filtered off to afford 0.047 g (73% of yield) of the expected product.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08536165B2uspto-grants-2013_09