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Citric Acid → 7-(3-Oxobutyl)imidazo[1,2-a]pyridine-3-carboxylic acid

HRID 570335
Notes
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Reaction equation

HRID 570335 reaction equation
[O:1]=[C:2]([CH3:19])[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][N:8]2[C:11]([C:14]([O:16]CC)=[O:15])=[CH:12][N:13]=[C:7]2[CH:6]=1.[Li+].[OH-].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CO>[O:1]=[C:2]([CH3:19])[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][N:8]2[C:11]([C:14]([OH:16])=[O:15])=[CH:12][N:13]=[C:7]2[CH:6]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 311Citric AcidHCID 3939Lithium HydroxideHCID 71280713HCID 71280713, compound

Product 1

HCID 712808037-(3-Oxobutyl)imidazo[1,2-a]pyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A stirring mixture of ethyl 7-(3-oxobutyl)imidazo[1,2-a]pyridine-3-carboxylate (85) (90 mg, 0.346 mmol) and 2N LiOH (0.5 mL) in THF:MeOH (4:1, 3 mL) was heated at 60° C. for 45 minutes. The reaction was cooled to room temperature and the pH was adjusted between 3-5 with 10% citric acid. The solvent was partially concentrated and the crude product was purified by reverse phase preparative HPLC to yield 7-(3-oxobutyl)imidazo[1,2-a]pyridine-3-carboxylic acid (86). MS m/z 233.08 (M+1)+.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. concentrationThe solvent was partially concentrated
  3. customthe crude product was purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-9f5d40fa190b47cf9005ddca1de67e29
Source dataset
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09023839B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes