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

HRID 1844187Notes

Reaction equation

[F:1][C:2]1[C:3]([CH2:8][O:9][C:10]2[C:11]3[N:12]([C:17]([C:21]([O:23]CC)=[O:22])=[C:18]([CH3:20])[N:19]=3)[CH:13]=[C:14]([CH3:16])[CH:15]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[OH-].[Li+].[ClH:28]>C1COCC1.CO>[ClH:28].[F:1][C:2]1[C:3]([CH2:8][O:9][C:10]2[C:11]3[N:12]([C:17]([C:21]([OH:23])=[O:22])=[C:18]([CH3:20])[N:19]=3)[CH:13]=[C:14]([CH3:16])[CH:15]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 40 °C

Procedure

24.06 g (70.1 mmol) of ethyl 8-[(3-fluoropyridin-2-yl)methoxy]-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylate from Example 120A were initially charged in 1.5 l of THF/methanol (5:1), 350.4 ml (350.4 mmol) of 1 N aqueous lithium hydroxide solution were added and the reaction mixture was stirred at 40° C. for 2.5 h. After cooling, the pH was adjusted to about 4 using 1 N aqueous hydrochloric acid and the solution was freed from THF/methanol under reduced pressure. The residue was cooled and the precipitated solid was filtered off and dried under reduced pressure. This gave 22.27 g (100% of theory) of the title compound.

Workup

temperatureAfter cooling
temperatureThe residue was cooled
filtrationthe precipitated solid was filtered off
customdried under reduced pressure

Sources & evidence

ORD record: ord-a95782f87f71400b9cc7e1ee09359257
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946215B2

Reaction notes

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