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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 388059Generated: October 30, 2026

Diethylamine → HCID 58931308, compound

https://huagongshe.com/reaction/388059

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiethylamineHCID 8021—
ReactantPotassium CarbonateHCID 11430—
ReactantGlycidyl tosylate, (R)-HCID 154187—
ReactantHCID 135829396HCID 135829396—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
SolventTetrahydrofuran ethyl acetateHCID 21939870—
ProductHCID 58931308HCID 5893130849.3%

Reaction Conditions

Temperature60 °C

Reaction Steps

After adding (2R)oxiran-2-ylmethyl 4-methyl-1-benzenesulfonate (66 mg, 0.290 mmol), potassium carbonate (32 mg, 0.231 mmol) and dimethylformamide (2 ml) to N6-ethyl-4-(3-chloro-4-(((methylamino)carbonyl)amino)phenoxy)-7-hydroxy-6-quinolinecarboxamide (80.0 mg, 0.193 mmol), the mixture was stirred at 60° C. for 7 hours. Diethylamine (1 ml) was then added, and the mixture was stirred at 60° C. overnight. The reaction solution was distributed between ethyl acetate-tetrahydrofuran (1:1) and water, and the organic layer was washed with water and saturated saline and then dried over anhydrous sodium sulfate. The solvent was distilled off, the residue was subjected to silica gel column chromatography (eluent-ethyl acetate:methanol=95:5), the fraction containing the target substance was concentrated, and crystals were precipitated from ethyl acetate-hexane (1:1), filtered out and blow-dried to obtain the title compound (51.7 mg, 0.095 mmol, 49.3%) as white crystals.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08372981B2
Source datasetuspto-grants-2013_02
ORD IDord-765c259fcfd54189b766ce58123d262a
Source noteuspto-grants-2013_02