Abstract
A simple and novel route for synthesis of new spirocyclic amide derivative is developed. The present work involves the oxidative cleavage of tert-butyl 1-(furan-2-yl)-4-oxo-2,3,7-triazaspiro[4.5]dec-1-ene-7-carboxylate 1 followed by the amine coupling and deprotection of Boc.
Highlights
Spirocyclic structures are found in wide range of natural compounds isolated from various sources.Spiro compounds are known to be PDE7 inhibitors and have a number of therapeutic applications in the treatment of pain, especially neuropathic pain
Two sharp bands at 1731 and 1660 cm−1 were due to pyrazolone carbonyl and amide carbonyl group respectively
A singlet observed at δ 12.50 ppm was due to the proton of amide NH
Summary
Spirocyclic structures are found in wide range of natural compounds isolated from various sources.Spiro compounds are known to be PDE7 inhibitors and have a number of therapeutic applications in the treatment of pain, especially neuropathic pain. The title compound, N-(3,4-dimethoxyphenyl)-4-oxo-2,3,7-triazaspiro[4.5]dec-1-ene-1-carboxamide hydrochloride (3), was prepared by the coupling of 7-(tert-butoxycarbonyl)-4-oxo-2,3,7triazaspiro[4.5]dec-1-ene-1-carboxylic acid (2) with 3,4-dimethoxyaniline using O-(7-azabenzotriazol1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU) followed by deprotection of Boc group using HCl in 1,4-dioxane (Scheme 1). The intermediate 2 was in turn prepared by the oxidative cleavage of tert-butyl 1-(furan-2-yl)-4-oxo-2,3,7-triazaspiro[4.5]dec-1-ene-7-carboxylate 1. The IR spectrum of compound (3) showed a wide absorption band at 3378 cm−1 due to the presence of NH groups in the molecule.
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