Synthesis of a hexahydropyrimido[1,2-a]azepine-2-carboxamide derivative useful as an HIV integrase inhibitor |
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Authors: | Marco Ferrara Benedetta Crescenzi Monica Donghi Ester Muraglia Emanuela Nizi Silvia Pesci Vincenzo Summa Cristina Gardelli |
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Institution: | Department of Medicinal Chemistry, IRBM-MRL Rome, Via Pontina, Km 30600, 00040 Pomezia (Rome), Italy |
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Abstract: | The hexahydropyrimido1,2-a]azepine-2-carboxamide derivative 1 could be obtained by three synthetic strategies, which allowed access to multigram amounts of material of high purity and ee. Two strategies involved alternative approaches to the bicyclic pyrimidone core, with the most efficient one being a two-step sequence from commercially available starting materials exploiting a little precedented cyclisation reaction. The remaining steps to 1 included an efficient crystallisation of an intermediate as a single stereoisomer. An alternative strategy employing a chiral starting material led to products of low optical purity but allowed the assignment of the configuration of the stereogenic centre of 1. |
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Keywords: | Hexahydropyrimido[1 2-a]azepine Integrase inhibitor 1 2 4-Oxadiazoline Amidoxime |
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