Abstract
A simple and novel route for the synthesis of new spirocyclic propionamide derivative is developed. The present work involves N-arylation of pyrazolone (1) using copper(I) iodide catalyst followed by reduction to give amine (2). The coupling of 2 with 3-(4-fluorophenyl)propionic acid and deprotection of Boc group yields the title compound (3).
Highlights
Spirocyclic structures are found in wide range of natural compounds isolated from various sources [1,2]
The title compound, 3-(4-fluorophenyl)-N-[4-(4-furan-2-yl-1-oxo-2,3,7-triazaspiro[4.5]dec-3-en-2yl)phenyl]propionamide hydrochloride (3) was prepared by the coupling of tert-butyl 3-(4-aminophenyl)1-(furan-2-yl)-4-oxo-2,3,7-triazaspiro[4.5]dec-1-ene-7-carboxylate (2) with 3-(4-fluorophenyl)-propionic acid using HATU followed by deprotection of Boc group using HCl in 1,4-dioxane (Scheme 1)
The intermediate 2 in turn prepared by N-arylation of tert-butyl 1-(furan-2-yl)-4-oxo-2,3,7triazaspiro[4.5]dec-1-ene-7-carboxylate (1) using copper(I) iodide catalyst followed by reduction
Summary
Spirocyclic structures are found in wide range of natural compounds isolated from various sources [1,2]. The title compound, 3-(4-fluorophenyl)-N-[4-(4-furan-2-yl-1-oxo-2,3,7-triazaspiro[4.5]dec-3-en-2yl)phenyl]propionamide hydrochloride (3) was prepared by the coupling of tert-butyl 3-(4-aminophenyl)1-(furan-2-yl)-4-oxo-2,3,7-triazaspiro[4.5]dec-1-ene-7-carboxylate (2) with 3-(4-fluorophenyl)-propionic acid using HATU followed by deprotection of Boc group using HCl in 1,4-dioxane (Scheme 1). The intermediate 2 in turn prepared by N-arylation of tert-butyl 1-(furan-2-yl)-4-oxo-2,3,7triazaspiro[4.5]dec-1-ene-7-carboxylate (1) using copper(I) iodide catalyst followed by reduction.
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