Preparation of the HIV Attachment Inhibitor BMS-663068. Part 4. Synthesis of the 6-Azaindole Core,Organic Process Research & Development

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Preparation of the HIV Attachment Inhibitor BMS-663068. Part 4. Synthesis of the 6-Azaindole Core
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2017-08-09 00:00:00 , DOI: 10.1021/acs.oprd.7b00152
Michael S. Bultman ₁ , Junying Fan ₁ , Dayne Fanfair ₁ , Michelle Soltani ₁ , James Simpson ₁ , Saravanababu Murugesan ₁ , Maxime Soumeillant ₁ , Ke Chen ₁ , Christina Risatti ₁ , Thomas E. La Cruz ₁ , Frederic G. Buono ₁ , Victor Hung ₁ , Richard L. Schild ₁ , Sabrina Ivy ₁ , Jason T. Sweeney ₁ , David A. Conlon ₁ , Martin D. Eastgate ₁

Affiliation

We report research focused on the construction of the 6-azaindole core, a key intermediate in the synthesis of the clinical candidate BMS-663068. The work describes an efficient and scalable method to access the 6-azaindole from a protected 3-ketopyrrole via a Pictet–Spengler cyclization and a radical-mediated aromatization. The process reported herein has been successfully implemented on the multikilogram scale to support preclinical development and clinical studies of BMS-663068.

中文翻译：

HIV附着抑制剂BMS-663068的制备。第4部分。6-氮杂吲哚核的合成

我们报告的研究集中在6-氮杂吲哚核心的建设，这是临床候选药物BMS-663068合成中的关键中间体。该工作描述了一种有效且可扩展的方法，该方法可通过Pictet-Spengler环化作用和自由基介导的芳构化作用从受保护的3-酮吡咯中访问6-氮杂吲哚。本文报道的方法已成功在多千克规模上实施，以支持BMS-663068的临床前开发和临床研究。

更新日期：2017-08-09

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