Citric Acid → HCID 71280525, compound

HRID 405836Notes

Reaction equation

HRID 405836 reaction equation
[CH3:1][C:2]1[S:3][C:4]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]([C:14]([C:17]([O:19]CC)=[O:18])=[CH:15][N:16]=3)[CH:13]=2)=[C:5]([CH3:7])[N:6]=1.[Li+].[OH-].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CO>[CH3:1][C:2]1[S:3][C:4]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]([C:14]([C:17]([OH:19])=[O:18])=[CH:15][N:16]=3)[CH:13]=2)=[C:5]([CH3:7])[N:6]=1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 3939Lithium HydroxideHCID 71280478HCID 71280478, compound

Product 1

HCID 71280525HCID 71280525, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of ethyl 6-(2,4-dimethylthiazol-5-yl)imidazo[1,2-a]pyridine-3-carboxylate (145) (190 mg, 0.630 mmol) and 2N LiOH (1 mL) in THF:MeOH (4:1, 4 mL) was heated at 60° C. for 30 minutes. The reaction was cooled to room temperature and the pH was adjusted between 4-5 with 10% citric acid. The solvent was partially reduced and the resulting solid was collected by vacuum filtration to give 6-(2,4-dimethylthiazol-5-yl)imidazo[1,2-a]pyridine-3-carboxylic acid (146). 1H NMR (400 MHz, d6-DMSO) δ 9.34 (s, 1H), 8.29 (s, 1H), 7.87 (dd, J=0.8, 9.2 Hz, 1H), 7.62 (dd, J=2.0, 9.2 Hz, 1H), 2.66 (s, 3H), 2.41 (s, 3H). MS m/z 274.06 (M+1)+.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationthe resulting solid was collected by vacuum filtration

Sources & evidence

ORD record
ord-5b75361cd2ce4227bf4837e4552b28f2
Source dataset
uspto-grants-2014_06
Patent number
US08754071B2

Reaction notes

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