Citric Acid → 6-(2-Cyanoethyl)imidazo[1,2-a]pyridine-3-carboxylic acid

HRID 405814Notes

Reaction equation

[C:1]([CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]2[N:9]([C:11]([C:14]([O:16]CC)=[O:15])=[CH:12][N:13]=2)[CH:10]=1)#[N:2].[Li+].[OH-].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CO>[C:1]([CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]2[N:9]([C:11]([C:14]([OH:16])=[O:15])=[CH:12][N:13]=2)[CH:10]=1)#[N:2]

Participants

Conditions

Temperature: 50 °C

Procedure

A stirring mixture of ethyl 6-(2-cyanoethyl)imidazo[1,2-a]pyridine-3-carboxylate (74) (100 mg, 0.411 mmol) and 2N LiOH (0.2 mL) in THF:MeOH (4:1, 3 mL) was heated at 50° 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 reduced. The resulting solid was collected by vacuum filtration and washed with excess water. Crude 6-(2-cyanoethyl)imidazo[1,2-a]pyridine-3-carboxylic acid (75) was dried and used in the next step without further purification. MS m/z 416.07 (M+1)+.

Workup

temperatureThe reaction was cooled to room temperature
filtrationThe resulting solid was collected by vacuum filtration
washwashed with excess water
dry with materialCrude 6-(2-cyanoethyl)imidazo[1,2-a]pyridine-3-carboxylic acid (75) was dried
customused in the next step without further purification

Sources & evidence

ORD record: ord-5ec9d5d96b114f918cc9cb3efea7cd1f
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754071B2

Reaction notes

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