K. Prasad
2021
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Abstract
A series of novel 1-(8-(ayloxy)-2-(trifluoromethyl)imidazo[1,2-a]pyrazin-6-yl)ethan-1-amine derivatives (11a-h) were synthesized by the O-alkylation of 1-(8-chloro-2-(trifluoromethyl) imidazo[1,2-a]pyrazin-6-yl)ethan-1-amine (9) with corresponding aryl alcohols (10a-h) in the presence of K2CO3. Reacion of commercially available ethyl 2-amino-2- thioxoacetate with triethyl oxonium hexafluoro phosphate gave ethyl 2-(ethylthio)-2-iminoacetat, which was reacted with 3-amino-1,1,1-trifluoropropan-2-one hydrochloride to afford ethyl 4-(trifluoromethyl)-1H-imidazole-2-carboxylate. Protection of (tert-butoxycarbonyl) alanine with ethyl chloroformate, and treated with diazomehane obtained tertbutyl (4-diazo-3-oxobutan-2-yl) carbamate. Tert-butyl (4-bromo-3-oxobutan-2-yl) carbamate was obtained by the reaction of compound 5 with 48% hydrogen bromide. Compound 3 was treated with compound to give 1-(3-((tertbutoxycarbonyl) amino)-2-oxobutyl)-4-(trifluoromethyl)-1H-imidazole-2-carboxylic acid. Cyclizaion of compound using ammonium bicarbonate gave tert-butyl (1-(8-oxo-2-(trifluoromethyl)-7,8-dihydroimidazo[1,2-a]pyrazin-6-yl) ethyl) carbamate, which was chlorinated by phosphorus oxychloride afforded 1-(8-chloro-2-(trifluoromethyl) imidazo [1,2-a]pyrazin-6-yl) ethan-1-amine. All the newly synthesized compounds were characterized by analytical spectral techniques, like 1H NMR, and LCMS, and also evaluated their antibacterial activity.