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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1644191Generated: October 29, 2026

Sodium hydride → 5-Bromo-1-methyl-3-[5-(4-methyl-piperazine-1-carbonyl)-pyridin-2-ylamino]-1H-pyridin-2-one

https://huagongshe.com/reaction/1644191

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium hydrideHCID 24758—
Reactant1-(6-Chloropyridine-3-carbonyl)-4-methylpiperazineHCID 902040—
Reactant3-Amino-5-bromo-1-methyl-1,2-dihydropyridin-2-oneHCID 52911268—
SolventDimethylformamideHCID 6228—
Product5-Bromo-1-methyl-3-[5-(4-methyl-piperazine-1-carbonyl)-pyridin-2-ylamino]-1H-pyridin-2-oneHCID 5921644126%

Reaction Steps

To a solution of (6-Chloro-pyridin-3-yl)-(4-methyl-piperazin-1-yl)-methanone (2.00 g, 7.46 mmol) in 10 mL dimethylformamide was added 3-Amino-5-bromo-1-methyl-1H-pyridin-2-one (1.80 g, 8.95 mmol) and sodium hydride (537 mg, 22.4 mmol). After stirring for 18 hours, this was quenched with water. This was extracted with ethylacetate. The ethylacetate layer was dried over anhydrous sodium sulfate, concentrated in vacuo, and purified by flash chromatography (gradient elution 0 to 5% methanol/dichloromethane) to yield 5-Bromo-1-methyl-3-[5-(4-methyl-piperazine-1-carbonyl)-pyridin-2-ylamino]-1H-pyridin-2-one (900 mg, 1.94 mmol). MS (ESI) 406.0 (M+H)+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08124604B2
Source datasetuspto-grants-2012_02
ORD IDord-a12265c1f6944105821abdb27f8557be
Source noteuspto-grants-2012_02