Hydrochloric Acid → 8-(1,3-Oxazol-5-yl)-6-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxylic acid

HRID 931012Notes

Reaction equation

[O:1]1[C:5]([C:6]2[C:7]3[N:8]([C:16]([C:19]([O:21]CC)=[O:20])=[CH:17][N:18]=3)[CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=2)=[CH:4][N:3]=[CH:2]1.C1COCC1.[OH-].[Na+].Cl>O.CCO>[O:1]1[C:5]([C:6]2[C:7]3[N:8]([C:16]([C:19]([OH:21])=[O:20])=[CH:17][N:18]=3)[CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=2)=[CH:4][N:3]=[CH:2]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixture of ethyl 8-(1,3-oxazol-5-yl)-6-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxylate (2.47 g), THF (75 mL) and EtOH (25 mL) was added 8N aqueous sodium hydroxide solution (1.42 mL), and the mixture was stirred at 50° C. for 4 hr. To the reaction mixture was added 1N hydrochloric acid at 0° C., and the mixture was diluted with water. The insoluble substance was collected by filtration, and washed with cooled IPE to give the title compound (2.21 g).

Workup

filtrationThe insoluble substance was collected by filtration
washwashed with cooled IPE

Sources & evidence

ORD record: ord-3949fcc8bebb48e6adf9106ff08c2e4d
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296746B2

Reaction notes

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