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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 512514Generated: November 2, 2026

Potassium Carbonate → 1-[4-Cyano-2-(propane-1-sulfonyl)-benzyl]-6-methyl-4-oxo-5-(3-trifluoromethyl-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid methylamide

https://huagongshe.com/reaction/512514

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPotassium CarbonateHCID 11430—
ReactantL-ProlineHCID 145742—
ReactantSodium propane-1-sulfinateHCID 23706191—
Reactant1-(2-Bromo-4-cyano-benzyl)-6-methyl-4-oxo-5-(3-trifluoromethyl-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid methylamideHCID 86711559—
CatalystCopper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 24350—
SolventDimethyl SulfoxideHCID 679—
Product1-[4-Cyano-2-(propane-1-sulfonyl)-benzyl]-6-methyl-4-oxo-5-(3-trifluoromethyl-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid methylamideHCID 86711558—

Reaction Conditions

Temperature110 °C

Reaction Steps

A mixture of preparation 25a (70 mg, 139 μmol), sodium 1-propylsulfinate (54 mg, 415 μmol), L-proline (20 mg, 174 μmol), CuI (7 mg, 37 μmol), K2CO3 (24 mg, 174 μmol) in DMSO (0.7 mL) is heated 60 min at 110° C. The reaction mixture is purified by preparative reversed-phase HPLC (XBridge, gradient of methanol in water, 0.3% NH4OH, 60° C.). Yield: 11 mg (15% of theory); ESI mass spectrum: [M+H]+=532; Retention time HPLC: 1.06 min (Z003—001).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09102624B2
Source datasetuspto-grants-2015_08
ORD IDord-92cbf3b37c1f47b6830f4878d6dca008
Source noteuspto-grants-2015_08