Hydrochloric Acid → HCID 68686803, compound

HRID 2238657Notes

Reaction equation

[C:1]([C:3]1[C:4]([C:22]2[N:26]3[CH:27]=[CH:28][CH:29]=[C:30]([CH:31]([F:33])[F:32])[C:25]3=[N:24][CH:23]=2)=[N:5][C:6]([NH:9][CH:10]([C:12]2[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=2)[C:15]([O:17]C)=[O:16])[CH3:11])=[N:7][CH:8]=1)#[N:2].CO.[OH-].[Na+].Cl>O1CCCC1>[C:1]([C:3]1[C:4]([C:22]2[N:26]3[CH:27]=[CH:28][CH:29]=[C:30]([CH:31]([F:32])[F:33])[C:25]3=[N:24][CH:23]=2)=[N:5][C:6]([NH:9][CH:10]([C:12]2[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=2)[C:15]([OH:17])=[O:16])[CH3:11])=[N:7][CH:8]=1)#[N:2]

Participants

Conditions

Temperature: 50 °C

Procedure

370 mg of the methyl 3-[1-({5-cyano-4-[8-(difluoromethyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl}amino)ethyl]benzoate [100-3] was suspended in a mixture solvent of 6 mL of methanol and 6 mL of tetrahydrofuran, then 4.15 mL of 1N aqueous solution of sodium hydroxide was added, and stirred at 50° C. for 30 minutes. Under an ice-cold condition, 825 μL of 5N hydrochloric acid was added, then the reaction solution was neutralized and concentrated under reduced pressure. The obtained residue was purified by preparative reversed phase liquid chromatography, and 216 mg of 3-[1-({5-cyano-4-[8-(difluoromethyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl}amino)ethyl] benzoic acid [100-4] was obtained as a pale yellow solid.

Workup

concentrationconcentrated under reduced pressure
customThe obtained residue was purified by preparative reversed phase liquid chromatography

Sources & evidence

ORD record: ord-00e7dec5a720411cb60ea19f924a9245
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07718801B2

Reaction notes

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