Development of a Safe and Scalable Method to Prepare 3-Bromo-N-alkyl-1,6-naphthyridones via Enamine Cyclization,Organic Process Research & Development

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Development of a Safe and Scalable Method to Prepare 3-Bromo-N-alkyl-1,6-naphthyridones via Enamine Cyclization
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2024-03-29 , DOI: 10.1021/acs.oprd.3c00479
Thomas Carr ₁ , Sam Beddoe ₁ , Stephen Johns ₁ , Jonathan Hull ₁ , Tom Stowe ₁ , Jonathan Moore ₁ , James Brown ₁ , Adrian Maddaford ₁ , Etienne Rochette ₂ , Michel Bernatchez ₂ , Martin Jean ₂ , Jean Francois Parent ₂ , Connor Barrett ₃ , Jeffrey B. Sperry ₃ , Daniel Richter ₃

Affiliation

A safe and efficient method to make N-alkyl-1,6-naphthyridones from primary amines is described. Due to issues with existing methodology involving strong exotherms and harsh reagents (triazine/alkyl halides), to prepare N-alkyl-1,6-naphthyridones, a method was developed that avoids these hazardous reagents and conditions. The developed route involved the preparation of a key enamine intermediate as a stable and isolatable solid, which could then undergo cyclization with primary amines to afford a variety of N-alkyl-1,6-naphthyridones that are of high interest in the preparation of pharmaceutically relevant molecules.

中文翻译：

开发一种通过烯胺环化制备 3-溴-N-烷基-1,6-萘啶酮的安全且可扩展的方法

描述了一种从伯胺制备N-烷基-1,6-萘啶酮的安全有效的方法。由于现有方法存在涉及强放热和刺激性试剂（三嗪/烷基卤化物）的问题，为了制备N-烷基-1,6-萘啶酮，开发了一种避免这些危险试剂和条件的方法。所开发的路线涉及将关键的烯胺中间体制备为稳定且可分离的固体，然后可以与伯胺进行环化，得到各种N-烷基-1,6-萘啶酮，这些酮在药物的制备中具有高度的意义。相关分子。

更新日期：2024-03-29

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