Hydrochloric Acid → (2-Chloro-4-imidazo[4,5-b]pyridin-3-yl-phenyl)-acetic acid

HRID 1010723Notes

Reaction equation

HRID 1010723 reaction equation
C([O:3][C:4](=[O:22])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:16]3=[N:17][CH:18]=[CH:19][CH:20]=[C:15]3[N:14]=[CH:13]2)=[CH:8][C:7]=1[Cl:21])C.[Li+].[OH-].Cl>C1COCC1>[Cl:21][C:7]1[CH:8]=[C:9]([N:12]2[C:16]3=[N:17][CH:18]=[CH:19][CH:20]=[C:15]3[N:14]=[CH:13]2)[CH:10]=[CH:11][C:6]=1[CH2:5][C:4]([OH:22])=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67021312HCID 67021312, compound

Product 1

HCID 67021590(2-Chloro-4-imidazo[4,5-b]pyridin-3-yl-phenyl)-acetic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.325 g (2-chloro-4-imidazo[4,5-b]pyridin-3-yl-phenyl)-acetic acid ethyl ester and 2 ml of 0.5 N aqueous solution of LiOH in 2 ml of THF is stirred for 1 hour at 40 C. The mixture obtained is allowed to cool to rt and an acidic pH is adjusted by addition of 0.5 N HCl aqueous solution. A precipitate forms and is collected by vacuum filtration. (2-Chloro-4-imidazo[4,5-b]pyridin-3-yl-phenyl)-acetic acid is obtained in the form of a solid. ES-MS: 288.0 [M+H]+; single peak at tR=3.00 min (System 1).

Workup

  1. customThe mixture obtained
  2. filtrationA precipitate forms and is collected by vacuum filtration

Sources & evidence

ORD record
ord-2f9ba899778e43cd9c6575e8ba99c396
Source dataset
uspto-grants-2011_07
Patent number
US07977338B2

Reaction notes

Loading…