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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1010463Generated: October 30, 2026

Dimethylformamide → N-(4-(6-Cyano-7-((2R)-oxiran-2-yl)methoxyquinolin-4-yloxy)-2,3-dimethylphenyl)-N'-cyclopropylurea

https://huagongshe.com/reaction/1010463

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantPotassium CarbonateHCID 11430—
ReactantGlycidyl tosylate, (R)-HCID 154187—
ReactantHCID 135829394HCID 135829394—
SolventWaterHCID 962—
SolventEthyl AcetateHCID 8857—
ProductN-(4-(6-Cyano-7-((2R)-oxiran-2-yl)methoxyquinolin-4-yloxy)-2,3-dimethylphenyl)-N'-cyclopropylureaHCID 8659148349.6%

Reaction Conditions

Temperature50 °C

Reaction Steps

Dimethylformamide (4 ml) was added to N-(2,3-dimethyl-4-(6-cyano-7-hydroxy-quinolin-4-yloxy)-phenyl)-N′-cyclopropylurea (476 mg), and then (2R)-(−)-glycidyl p-toluenesulfonate (365 mg) and potassium carbonate (340 mg) were further added and the mixture was heated at 50° C. for 4 hours. Water was added to the reaction solution, extraction was performed with ethyl acetate, the organic layer was washed with water and saturated brine in that order and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained crude product was washed with ethyl acetate to obtain the title compound (270 mg) as light yellow crystals.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07973160B2
Source datasetuspto-grants-2011_07
ORD IDord-e21f40a0fdcb4c9d93ae28f1d13ed262
Source noteuspto-grants-2011_07