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

HRID 1624087Notes

Reaction equation

[F:1][C:2]1[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:17]([C:21]([O:23]CC)=[O:22])=[C:18]([CH3:20])[N:19]=2)[CH:9]=[C:10]([N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:11]=1.[OH-].[Li+].Cl>C1COCC1.CO>[F:30][C:26]1[CH:27]=[CH:28][CH:29]=[C:2]([F:1])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:17]([C:21]([OH:23])=[O:22])=[C:18]([CH3:20])[N:19]=2)[CH:9]=[C:10]([N:12]2[CH2:13][CH2:14][CH2:15][CH2:16]2)[CH:11]=1

Participants

Conditions

Temperature: 40 °C

Procedure

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).

Workup

additionwere added
temperatureThe mixture was cooled
concentrationconcentrated
additionWater was added to the solid
customformed
customthe product was triturated
filtrationfiltered off with suction
washwashed with water
customdried under reduced pressure

Sources & evidence

ORD record: ord-61dd729e845d43ecbe0178bdbbc8671d
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778964B2

Reaction notes

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