Syntheses of aza and fluorine-substituted 3-(piperidin-4-yl)-4, 5-dihydro-1H-benzo [d][1, 3] diazepin-2 (3H)-ones

…, RL Civiello, SE Mercer, JE Macor, GM Dubowchik

Index: Han, Xiaojun; Civiello, Rita L.; Mercer, Stephen E.; Macor, John E.; Dubowchik, Gene M. Tetrahedron Letters, 2009 , vol. 50, # 4 p. 386 - 388

Full Text: HTML

Citation Number: 14

Abstract

A practical and expedient synthesis of the title compounds is described. They were prepared by Stille reaction of nitro halopyridines 4 or nitro fluro-halobenzenes 10, followed by Michael addition of tert-butyl 4-aminopiperidine-1-carboxylate to the resulting activated vinyl compounds 5 and 11, hydrogenation (–NO2→–NH2), cyclic urea formation, Boc removal, and HCl salt formation. However, N3 and F1 analogs could not be made by this general ...