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

HRID 706584

Reaction equation

[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][N:16]3[C:19]([C:22]([O:24]CC)=[O:23])=[CH:20][N:21]=[C:15]3[CH:14]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].O.[OH-].[Li+:29].Cl>O>[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][N:16]3[C:19]([C:22]([O-:24])=[O:23])=[CH:20][N:21]=[C:15]3[CH:14]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[Li+:29]

Participants

Conditions

Temperature: 95 °C

Procedure

To ethyl 7-(2-(4-isopropylpiperazin-1-yl)ethoxy)imidazo[1,2-a]pyridine-3-carboxylate (5.68 g, 15.8 mmol) in water (30 mL) was added lithium hydroxide hydrate (0.67 g, 16.0 mmol). The reaction was heated to 95° C. for 4 hours. The reaction was cooled to ambient temperature and hydrogen chloride (0.0394 mL, 4M in dioxane) was added to the reaction mixture, which was stirred for 10 minutes. Water was removed under vacuum for overnight to give the title compound (5.43 g).

Workup

temperatureThe reaction was cooled to ambient temperature
customWater was removed under vacuum for overnight

Sources & evidence

ORD record: ord-fd16f69b92e44f76a9f2af8afb2e4539
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174981B2

Linked notes

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