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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2203010Generated: November 3, 2026

Methyl iodide → 4-(((5-Chloro-2-thienyl)methyl)(methyl)amino)-1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)pyridin-2(1H)-one

https://huagongshe.com/reaction/2203010

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethyl iodideHCID 6328—
ReactantSodium hydrideHCID 24758—
Reactant4-(((5-Chloro-2-thienyl)methyl)amino)-1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)pyridin-2(1H)-oneHCID 89690193—
SolventDimethylformamideHCID 6228—
Product4-(((5-Chloro-2-thienyl)methyl)(methyl)amino)-1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)pyridin-2(1H)-oneHCID 89690369—

Reaction Conditions

Temperature0 °C

Reaction Steps

To a suspension of 4-(((5-chloro-2-thienyl)methyl)amino)-1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)pyridin-2(1H)-one (11.5 mg) in DMF (1 ml) was added NaH (60% in oil, 1.7 mg) at 0° C. After the reaction mixture was stirred at 0° C. for 10 min, iodomethane (2.61 μl) was added to the reaction mixture. The mixture was stirred at room temperature for 3 h. The mixture was quenched with water, and extracted with EtOAc. The organic layer was separated, washed with water and brine successively, dried over MgSO4 and concentrated in vacuo. The residue was triturated with IPE, and the resulting solid was collected by filtration and washed with EtOAc-IPE to give the title compound (4.0 mg) as a pale yellow solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09365540B2
Source datasetuspto-grants-2016_06
ORD IDord-80e5f09fdf0e49cda73d6bc7a8d09cc1
Source noteuspto-grants-2016_06