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

HRID 1844193Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1844193
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-ef5eb163bf454661966ba90f38cd757e
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946215B2

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