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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1990011Generated: October 27, 2026

Cesium carbonate → 3-{[3-chloro-5-(pyrrolidin-1-ylcarbonyl)pyridin-2-yl]oxy}-5-[(1-methylethyl)oxy]-N-(5-methylpyrazin-2-yl)benzamide

https://huagongshe.com/reaction/1990011

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCesium carbonateHCID 10796—
Reactant2,3-Dichloro-5-(pyrrolidin-1-ylcarbonyl)pyridineHCID 20113989—
Reactant3-Hydroxy-N-(5-methylpyrazin-2-yl)-5-[(propan-2-yl)oxy]benzamideHCID 59127162—
SolventAcetonitrileHCID 6342—
Product3-{[3-chloro-5-(pyrrolidin-1-ylcarbonyl)pyridin-2-yl]oxy}-5-[(1-methylethyl)oxy]-N-(5-methylpyrazin-2-yl)benzamideHCID 5362955073.1%

Reaction Conditions

Temperature120 °C

Reaction Steps

Cesium carbonate (782 mg, 2.4 mmol) was added to a solution of 3-hydroxy-5-[(1-methylethyl)oxy]-N-(5-methylpyrazin-2-yl)benzamide (230 mg, 0.8 mmol) and 2,3-dichloro-5-(pyrrolidin-1-ylcarbonyl)pyridine (234 mg, 0.96 mmol) in acetonitrile (5 mL) and the stirred mixture heated in a microwave reactor at 120° C. for 2 hours. The mixture was cooled to RT and the acetonitrile evaporated in vacuo. The residue was partitioned between water (25 mL) and ethyl acetate (50 mL), the organic layer washed with brine, dried (MgSO4) and evaporated to a residue which was chromatographed on silica, eluting with 75% ethyl acetate in isohexane, to give the desired compound (290 mg).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07642263B2
Source datasetuspto-grants-2010_01
ORD IDord-59e457d7b2844b99ae98ae1f87856d7a
Source noteuspto-grants-2010_01