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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1029144Generated: October 25, 2026

Diisopropylethylamine → 2,5-Dichloro-N-[4-(6-oxo-5,6-dihydro-benzo[c][1,8]naphthyridin-1-yloxy)-phenyl]-nicotinamide

https://huagongshe.com/reaction/1029144

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiisopropylethylamineHCID 81531—
Reactant2,5-Dichloro-nicotinoyl chlorideHCID 2799996—
Reactant1-(4-Amino-phenoxy)-5H-benzo[c][1,8]naphthyridin-6-oneHCID 58168367—
Solvent1,4-DioxaneHCID 31275—
SolventWater ethylacetateHCID 22728543—
Product2,5-Dichloro-N-[4-(6-oxo-5,6-dihydro-benzo[c][1,8]naphthyridin-1-yloxy)-phenyl]-nicotinamideHCID 5816832764.5%

Reaction Steps

Compound 137 (40 mg, 0.13 mmol), 2,5-dichloro-nicotinoyl chloride (28 mg, 0.13 mmol), and DIEA (0.02 mL, 0.13 mmol) were suspended in dioxane (2 mL), and stirred overnight at room temperature. The reaction mixture was diluted with EtOAc/H2O. The resulting precipitate was filtered, washed with EtOAc/H2O, and dried under vacuum to provide 180 (40 mg, 64% yield) as a white solid. LC-MS (M+H=478, obsd.=478).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08735584B2
Source datasetuspto-grants-2014_05
ORD IDord-6086b94094634432a2e6dc0c1eea5f42
Source noteuspto-grants-2014_05