Hydrochloric Acid → 3-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-ylcarbamoyl)imidazo[1,2-a]pyridine-7-carboxylic acid

HRID 79285Notes

Reaction equation

[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH:12][C:13]([C:15]2[N:19]3[CH:20]=[CH:21][C:22]([C:24]([O:26]CC)=[O:25])=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([CH3:36])[N:31]=2)[N:4]=1)[CH3:2].[OH-].[Li+].Cl.[Cl-].[Li+]>C1COCC1.O>[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH:12][C:13]([C:15]2[N:19]3[CH:20]=[CH:21][C:22]([C:24]([OH:26])=[O:25])=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([CH3:36])[N:31]=2)[N:4]=1)[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of ethyl 3-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-ylcarbamoyl)imidazo[1,2-a]pyridine-7-carboxylate (430 mg, 0.891 mmol) (Example 23) in THF/water (6 mL/1 mL) was added lithium hydroxide (21.3 mg, 0.89 mmol). The mixture was heated at 70° C. with stirring in a sealed tube for 2 hours. The mixture was allowed to cool and hydrogen chloride (0.45 mL, 4M in dioxane) was added. The solvent was removed under reduced pressure to give a mixture of the product and lithium chloride (410 mg) which was carried on directly to the next step.

Workup

temperatureto cool
customThe solvent was removed under reduced pressure
customto give

Sources & evidence

ORD record: ord-acbfcf4017434c4989a7fedd1f5d1b22
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841455B2

Reaction notes

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