Hydrochloric Acid → 8-[(3,5-Difluoropyridine-4-yl)methoxy]-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylic acid

HRID 1844193Notes

Reaction equation

HRID 1844193 reaction equation
[F:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([F:26])[C:7]=1[CH2:8][O:9][C:10]1[C:11]2[N:12]([C:17]([C:21]([O:23]CC)=[O:22])=[C:18]([CH3:20])[N:19]=2)[CH:13]=[C:14]([CH3:16])[CH:15]=1.[OH-].[Na+].Cl>O1CCOCC1>[F:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([F:26])[C:7]=1[CH2:8][O:9][C:10]1[C:11]2[N:12]([C:17]([C:21]([OH:23])=[O:22])=[C:18]([CH3:20])[N:19]=2)[CH:13]=[C:14]([CH3:16])[CH:15]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86718219Ethyl 8-[(3,5-difluoropyridine-4-yl)methoxy]-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylate

Product 1

HCID 867182208-[(3,5-Difluoropyridine-4-yl)methoxy]-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

5.34 g (14.78 mmol) of ethyl 8-[(3,5-difluoropyridine-4-yl)methoxy]-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylate from Example 130A were initially charged in 160 ml of dioxane, 147.8 ml (147.8 mmol) of 1 M aqueous sodium hydroxide solution were added and the mixture was stirred at RT overnight. The reaction mixture, cooled to RT, was adjusted to about pH 4 using 1 N aqueous hydrochloric acid, the solvent was concentrated to half of its original volume and the precipitated solid was filtered off with suction and dried under reduced pressure. This gave 4.61 g (93% of theory) of the target compound.

Workup

  1. temperatureThe reaction mixture, cooled to RT
  2. concentrationthe solvent was concentrated to half of its original volume
  3. filtrationthe precipitated solid was filtered off with suction
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-ef5eb163bf454661966ba90f38cd757e
Source dataset
uspto-grants-2015_02
Patent number
US08946215B2

Reaction notes

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