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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1844145Generated: October 31, 2026

Hydrochloric Acid → 8-[(2,6-Difluorobenzyl)oxy]-2-methyl-6-(pyrrolidin-1-yl)imidazo[1,2-a]pyridine-3-carboxylic acid

https://huagongshe.com/reaction/1844145

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
ReactantLithium HydroxideHCID 3939—
ReactantEthyl 8-[(2,6-difluorobenzyl)oxy]-2-methyl-6-(pyrrolidin-1-yl)imidazo[1,2-a]pyridine-3-carboxylateHCID 86718167—
SolventMeOH tetrahydrofuranHCID 21899815—
Product8-[(2,6-Difluorobenzyl)oxy]-2-methyl-6-(pyrrolidin-1-yl)imidazo[1,2-a]pyridine-3-carboxylic acidHCID 86718168—

Reaction Conditions

Temperature40 °C

Reaction Steps

90 mg of ethyl 8-[(2,6-difluorobenzyl)oxy]-2-methyl-6-(pyrrolidin-1-yl)imidazo[1,2-a]pyridine-3-carboxylate (Example 32A; 0.217 mmol, 1 equivalent) were dissolved in 6 ml of THF/methanol 5:1, 1.1 ml of 1N aqueous lithium hydroxide solution (1.1 mmol, 5 equivalents) were added and the mixture was warmed to 40° C. and stirred at this temperature for 20 h. The mixture was cooled, acidified to pH 4 with 6 N hydrochloric acid and concentrated. Water was added to the solid formed and the product was triturated, filtered off with suction, washed with water and dried under reduced pressure. This gave 87 mg of the title compound (93% of theory).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08946215B2
Source datasetuspto-grants-2015_02
ORD IDord-026fbe32981145d0b2868102c3dd17a4
Source noteuspto-grants-2015_02