Hydrochloric Acid → 2-(4-{4,4-Dimethyl-2,5-dioxo-3-[2-(pyridin-3-ylamino)pyridin-4-ylmethyl]imidazolidin-1-yl}-phenyl)-2-methylpropionic acid

HRID 546631Notes

Reaction equation

HRID 546631 reaction equation
[CH3:1][C:2]1([CH3:36])[C:6](=[O:7])[N:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([CH3:20])([CH3:19])[C:15]([O:17]C)=[O:16])=[CH:10][CH:9]=2)[C:4](=[O:21])[N:3]1[CH2:22][C:23]1[CH:28]=[CH:27][N:26]=[C:25]([NH:29][C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=2)[CH:24]=1.[OH-].[K+].Cl>CO.O>[CH3:1][C:2]1([CH3:36])[C:6](=[O:7])[N:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([CH3:19])([CH3:20])[C:15]([OH:17])=[O:16])=[CH:10][CH:9]=2)[C:4](=[O:21])[N:3]1[CH2:22][C:23]1[CH:28]=[CH:27][N:26]=[C:25]([NH:29][C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=2)[CH:24]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 57626005HCID 57626005, compound

Product 1

HCID 576259742-(4-{4,4-Dimethyl-2,5-dioxo-3-[2-(pyridin-3-ylamino)pyridin-4-ylmethyl]imidazolidin-1-yl}-phenyl)-2-methylpropionic acidYield 68.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 0.34 g of methyl 2-[4-(4,4-dimethyl-2,5-dioxo-3-{[2-(pyridin-3-ylamino)pyridin-4-yl]methyl}imidazolidin-1-yl)phenyl]-2-methylpropanoate obtained in stage e) below in 20 mL of methanol, at room temperature, are added 7 mL of 1N potassium hydroxide. The reaction medium is heated at reflux for two hours and concentrated under reduced pressure. The residue obtained is taken up in 10 mL of water and then acidified with 2N HCl to pH=5. The white solid formed is filtered off and then dried to give 0.225 g of 2-[4-(4,4-dimethyl-2,5-dioxo-3-{[2-(pyridin-3-ylamino)pyridin-4-yl]methyl}imidazolidin-1-yl)phenyl]-2-methylpropanoic acid, the characteristics of which are as follows:

Workup

  1. temperatureThe reaction medium is heated
  2. temperatureat reflux for two hours
  3. concentrationconcentrated under reduced pressure
  4. customThe residue obtained
  5. customThe white solid formed
  6. filtrationis filtered off
  7. customdried

Sources & evidence

ORD record
ord-60e06ad5799544b4931e40ef9dc47edd
Source dataset
uspto-grants-2011_05
Patent number
US07935819B2

Reaction notes

Loading…