Hydrochloric Acid → Lithium 7-(2-(4-methylpiperazin-1-yl)ethoxy)imidazo[1,2-a]pyridine-3-carboxylate

HRID 79479Notes

Reaction equation

[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][N:14]3[C:17]([C:20]([O:22]CC)=[O:21])=[CH:18][N:19]=[C:13]3[CH:12]=2)[CH2:4][CH2:3]1.O.[OH-].[Li+:27].Cl>O>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][N:14]3[C:17]([C:20]([O-:22])=[O:21])=[CH:18][N:19]=[C:13]3[CH:12]=2)[CH2:4][CH2:3]1.[Li+:27]

Participants

Conditions

Temperature: 95 °C

Procedure

To ethyl 7-(2-(4-methylpiperazin-1-yl)ethoxy)imidazo[1,2-a]pyridine-3-carboxylate (Preparation D; 43.93 g, 132.2 mmol) in H2O (150 mL) was added lithium hydroxide hydrate (6.31 g, 150.4 mmol). The reaction mixture was heated to 95° C. for 4 hours. The mixture was cooled to ambient temperature and hydrogen chloride (4.626 mL, 4M in dioxane) was added followed by stirring for 10 minutes. Water was removed under reduced pressure, and the residue was dried under vacuum for 16 hours to give the product, lithium 7-(2-(4-methylpiperazin-1-yl)ethoxy)imidazo[1,2-a]pyridine-3-carboxylate (42.78 g).

Workup

temperatureThe mixture was cooled to ambient temperature
customWater was removed under reduced pressure
customthe residue was dried under vacuum for 16 hours

Sources & evidence

ORD record: ord-4d72e38b79ef48ce99203520014e8a9b
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841455B2

Reaction notes

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