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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 228928Generated: October 26, 2026

Methanesulfonic Acid → 6-Methoxy-4-(6-methyl-2-thiazol-2-yl-pyridin-3-yloxy)-quinolin-7-ol

https://huagongshe.com/reaction/228928

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethanesulfonic AcidHCID 6395—
ReactantTrifluoroacetic acidHCID 6422—
ReactantSodium BicarbonateHCID 516892—
Reactant7-Benzyloxy-6-methoxy-4-(6-methyl-2-thiazol-2-yl-pyridin-3-yloxy)-quinolineHCID 23078276—
Product6-Methoxy-4-(6-methyl-2-thiazol-2-yl-pyridin-3-yloxy)-quinolin-7-olHCID 13585483171.7%

Reaction Conditions

Temperature80 °C

Reaction Steps

Trifluoroacetic acid (1 ml) and methanesulfonic acid (0.1 ml) were added to 7-benzyloxy-6-methoxy-4-(6-methyl-2-thiazol-2-yl-pyridin-3-yloxy)-quinoline (compound 328) (40 mg), and the mixture was stirred at 80° C. for 1.5 hr. The reaction solution was cooled to room temperature, and a saturated aqueous sodium hydrogencarbonate solution was then added to the reaction solution. The mixture was made alkaline, and the mixture was then extracted with chloroform. The chloroform layer was washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using chloroform-methanol to give the title compound (23 mg, yield 70%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07560558B2
Source datasetuspto-grants-2009_07
ORD IDord-9d4d47b277a343e7a631318ed8c396af
Source noteuspto-grants-2009_07