Open AccessDesign, Synthesis and Antibacterial Activity of N-(3-((4-(6-(2,2,2- Trifluoroethoxy)pyridin-3-yl)-1H-imidazol-2-yl)methyl)oxetan-3-yl)amide Derivatives
Author(s) -
B. S. R. Reddy,
K.R.S. Prasad
Publication year - 2021
Publication title -
asian journal of chemistry/asian journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.145
H-Index - 34
eISSN - 0975-427X
pISSN - 0970-7077
DOI - 10.14233/ajchem.2021.23039
Subject(s) - chemistry , amide , acetic acid , hydrochloride , proton nmr , ammonium acetate , medicinal chemistry , bromide , amine gas treating , catalysis , nuclear chemistry , organic chemistry , high performance liquid chromatography
A new series of N-(3-((4-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)-1H-imidazol-2-yl)methyl)oxetan-3-yl)amide derivatives (10a-h)were synthesized by the reaction of 3-((4-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)-1H-imidazol-2-yl)methyl)oxetan-3-amine (8) with various carboxylic acids in the presence ofT3P catalyst. The reaction is usually furnished within 60 min with good isolated yields. Coupling of6-(2,2,2-trifluoroethoxy) nicotinic acid (1) with Weinreb amine hydrochloride gave N-methoxy-Nmethyl-6-(2,2,2-trifluoroethoxy) nicotinamide (2). Compound 3 was synthesized by the Grignardreaction of compound 2 with methylmagnesium bromide. Bromination of compound 3 with N-bromosuccinamide to obtain 2-bromo-1-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethan-1-one (4), which wasreacted with 2-(3-(((benzyloxy)carbonyl)amino)oxetan-3-yl)acetic acid (5) gave 2-oxo-2-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl 2-(3-(((benzyloxy)carbonyl)amino)oxetan-3-yl)acetate (6).Compound 7 was synthesized by the cyclization of compound 6 with ammonium acetate. Finally,debenzylation of compound 7 gave 3-((4-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)-1H-imidazol-2-yl)methyl)oxetan-3-amine (8). All the synthesized amide compounds were characterized by analyticalspectral techniques, like 1H & 13C NMR and LCMS and also evaluated their antibacterial activity.