5-[2-(4-Methoxybenzylamino)pyridin-6-yl]pentanoic acid ethyl ester → 5-(2-Aminopyridin-6-yl)pentanoic acid ethyl ester

HRID 2187397Notes

Reaction equation

HRID 2187397 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[N:14]=[C:13]([NH:15]CC2C=CC(OC)=CC=2)[CH:12]=[CH:11][CH:10]=1)[CH3:2]>C(O)(C(F)(F)F)=O>[CH2:1]([O:3][C:4](=[O:25])[CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[N:14]=[C:13]([NH2:15])[CH:12]=[CH:11][CH:10]=1)[CH3:2]

Participants

3

Reactant 1

HCID 700925705-[2-(4-Methoxybenzylamino)pyridin-6-yl]pentanoic acid ethyl ester

Product 1

HCID 542733055-(2-Aminopyridin-6-yl)pentanoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The ester 16-3 (5.7 g) in TFA (75 mL) was heated at 60° C. for 2 hours then cooled and the excess TFA removed in vacuo. The residue was diluted with water, made basic with NaHCO3 and extracted with ether (3×). After washing the ether layer with saturated NaHCO3 then brine, it was dried (Na2SO4) and concentrated to give a viscous oil. Purification by silica gel chromatography (hexane:EtOAc 3:7) afforded the title compound 16-4 as an oil.

Workup

  1. temperaturethen cooled
  2. customthe excess TFA removed in vacuo
  3. additionThe residue was diluted with water
  4. extractionextracted with ether (3×)
  5. washAfter washing the ether layer with saturated NaHCO3
  6. dry with materialbrine, it was dried (Na2SO4)
  7. concentrationconcentrated
  8. customto give a viscous oil
  9. customPurification by silica gel chromatography (hexane:EtOAc 3:7)

Sources & evidence

ORD record
ord-647a2e460d0d41509e547cc9ac4adff4
Source dataset
uspto-grants-2002_06
Patent number
US06410526B1

Reaction notes

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