Ethyl 2-(3-aminophenoxy)acetate → (3-{[6-(4-Chloro-phenyl)-pyridine-2-carbonyl]-amino}-phenoxy)-acetic acid ethyl ester

HRID 2053267Notes

Reaction equation

HRID 2053267 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([C:14]([OH:16])=O)[CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH2:17]([O:19][C:20](=[O:30])[CH2:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([NH2:29])[CH:24]=1)[CH3:18]>CCOC(C)=O>[CH2:17]([O:19][C:20](=[O:30])[CH2:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([NH:29][C:14]([C:12]2[CH:11]=[CH:10][CH:9]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[N:13]=2)=[O:16])[CH:24]=1)[CH3:18]

Participants

4

Reactant 2

HCID 412308Ethyl 2-(3-aminophenoxy)acetateHCID 247301366-(4-Chlorophenyl)picolinic acid

Product 1

HCID 59654844(3-{[6-(4-Chloro-phenyl)-pyridine-2-carbonyl]-amino}-phenoxy)-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Carboxylic acid (149)(50 mg, 0.21 mmol) was coupled to aniline (64)(42 mg, 0.21 mmol) using Method C. During this reaction, partial hydrolysis occurred. The residue was re-dissolved in EtOAc (2 ml) and the organic layer was washed with 1M HCl (2×1 ml), dried (Na2SO4), filtered and the solvent removed in vacuo to give a mixture of acid and ester, which was used without further purification.

Workup

  1. customDuring this reaction, partial hydrolysis
  2. washthe organic layer was washed with 1M HCl (2×1 ml)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. customto give
  7. customwas used without further purification

Sources & evidence

ORD record
ord-73f1ae9d27c849558267f658cd21add7
Source dataset
uspto-grants-2008_02
Patent number
US07326732B2

Reaction notes

Loading…