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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 387940Generated: October 25, 2026

Cyclopropylamine → N-{4-[6-(Cyclopropylamino)carbonyl-7-methoxy-4-quinolyl]oxyphenyl}-N'-(4-fluorophenyl)urea

https://huagongshe.com/reaction/387940

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCyclopropylamineHCID 69828—
Reactant1-Hydroxybenzotriazole hydrateHCID 2796029—
Reactant1-(3-Diethylaminopropyl)-3-ethylcarbodiimide hydrochlorideHCID 9964512—
Reactant4-(4-(((4-Fluoroanilino)carbonyl)amino)phenoxy)-7-methoxy-6-quinolinecarboxylic acidHCID 22936350—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
SolventTriethylamineHCID 8471—
SolventEthyl AcetateHCID 8857—
ProductN-{4-[6-(Cyclopropylamino)carbonyl-7-methoxy-4-quinolyl]oxyphenyl}-N'-(4-fluorophenyl)ureaHCID 5893083644.5%

Reaction Steps

After dissolving the N-[4-(6-carboxy-7-methoxy-4-quinolyl)oxyphenyl]-N′-(4-fluorophenyl)urea (60 mg) synthesized in Example 341 in dimethylformamide (1.5 ml), there were added 1-ethyl-3-(3-diethylaminopropyl)-carbodiimide hydrochloride (39 mg), 1-hydroxy-1H-benzotriazole monohydrate (31 mg), triethylamine (30 μl) and cyclopropylamine (0.05 ml) and the mixture was stirred overnight at room temperature. The reaction solution was distributed between ethyl acetate and water, and the organic layer was washed with water and then dried over anhydrous sodium sulfate. After distilling off the solvent, crystals were precipitated with ethyl acetate, filtered out and dried under reduced pressure to obtain the title compound (29 mg) as white crystals.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08372981B2
Source datasetuspto-grants-2013_02
ORD IDord-3420ff75cd274140a16e1c02037ed533
Source noteuspto-grants-2013_02