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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 502682Generated: November 4, 2026

Triethylamine → N-cyclopropyl-4-methyl-3-(2-(6-(2-morpholinoethylamino)pyridin-3-yl)ethynyl)benzamide

https://huagongshe.com/reaction/502682

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
ReactantN-Cyclopropyl-3-iodo-4-methylbenzamideHCID 21914546—
Reactant5-ethynyl-N-(2-morpholinoethyl)pyridin-2-amineHCID 59427939—
CatalystCopper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 24350—
SolventEthyl AcetateHCID 8857—
Solvent1,4-DioxaneHCID 31275—
ProductN-cyclopropyl-4-methyl-3-(2-(6-(2-morpholinoethylamino)pyridin-3-yl)ethynyl)benzamideHCID 59427921—

Reaction Conditions

Temperature90 °C

Reaction Steps

5-Ethynyl-N-(2-morpholinoethyl)pyridin-2-amine (0.54 g, 2.36 mmol), N-cyclopropyl-3-iodo-4-methylbenzamide (0.71 g, 2.36 mmol), and triethylamine (0.49 mL, 3.54 mmol) were dissolved in dioxane (10 mL) before these were sparged with nitrogen for 15 min.; palladium dichloro-bis-triphenylphosphine (83 mg, 0.12 mmol) and copper (I) iodide (45 mg, 0.24 mmol) were added before the reaction mixture was heated to 90° C. for 6 h. The reaction mixture was diluted with 100 mL EtOAc, washed with 50 mL saturated, aqueous NaHCO3, and dried over anhydrous Na2SO4. After purification by chromatography, the title compound was obtained as a yellow oil. MS (ES+): 406 (M+H)+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07776869B2
Source datasetuspto-grants-2010_08
ORD IDord-24568232f9a744a1b5d17509f983f90f
Source noteuspto-grants-2010_08