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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1778113Generated: October 30, 2026

Dimethyl Sulfoxide → (racemic) N-(5-cyano-4-((2-methoxyethyl)amino)pyridin-2-yl)-7-formyl-6-((3-hydroxy-4-methyl-2-oxopiperazin-1-yl)methyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide

https://huagongshe.com/reaction/1778113

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethyl SulfoxideHCID 679—
Reactant4-((8-((5-Cyano-4-((2-methoxyethyl)amino)pyridin-2-yl)carbamoyl)-2-formyl-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)methyl)-1-methyl-3-oxopiperazine 1-oxideHCID 118036870—
Product(racemic) N-(5-cyano-4-((2-methoxyethyl)amino)pyridin-2-yl)-7-formyl-6-((3-hydroxy-4-methyl-2-oxopiperazin-1-yl)methyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamideHCID 118036487—

Reaction Steps

A solution of 4-((8-((5-cyano-4-((2-methoxyethyl)amino)pyridin-2-yl)carbamoyl)-2-formyl-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)methyl)-1-methyl-3-oxopiperazine 1-oxide (Example 222, 5 mg, 0.01 mmol) in DMSO (1 ml) was stirred at room temperature. After 30 h, the reaction mixture was concentrated and the residue purified by reverse phase chromatography: Atlantis C18 T3 column (3.5 um, 4.6×150 mm, 45° C.), eluting with 1:1 acetonitrile/water (containing 10 mM NH4OAc, 0.02% TFA). The product containing fraction was evaporated to give the title compound as a gray solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09266883B2
Source datasetuspto-grants-2016_02
ORD IDord-bf8bb4eb53fe4a99856be9fdb2fa355f
Source noteuspto-grants-2016_02