Hydrochloric Acid → HCID 71280499, compound

HRID 405816Notes

Reaction equation

HRID 405816 reaction equation
FC(F)O[C:4]1[CH:9]=[CH:8][N:7]2[C:10]([C:13]([O:15]CC)=[O:14])=[CH:11][N:12]=[C:6]2[CH:5]=1.[Li+].[OH-:20].Cl>C1COCC1.CO>[O:20]=[C:4]([CH3:9])[CH2:5][CH2:6][C:9]1[CH:4]=[CH:5][C:6]2[N:7]([C:10]([C:13]([OH:15])=[O:14])=[CH:11][N:12]=2)[CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 71280851HCID 71280851, compound

Product 1

HCID 71280499HCID 71280499, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A stirring mixture of ethyl 7-(difluoromethoxy)imidazo[1,2-a]pyridine-3-carboxylate (79) (150 mg, 0.585 mmol) and 2N LiOH (1 mL) in THF:MeOH (4:1, 5 mL) was heated at 60° C. for 45 minutes. The reaction was cooled to room temperature and the pH was adjusted between 4-5 with 1N HCl. The solvent was partially reduced and the crude product was purified by reverse phase preparative HPLC to yield 6-(3-oxobutyl)imidazo[1,2-a]pyridine-3-carboxylic acid (80). MS m/z 229.03 (M+1)+.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customthe crude product was purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-44b6f0b28e5b4651945cd65632842535
Source dataset
uspto-grants-2014_06
Patent number
US08754071B2

Reaction notes

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