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Development of Versatile Routes for the Preparation of an Intermediate to Immuno-Oncology Agonist BMS-986299
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2023-04-26 , DOI: 10.1021/acs.oprd.3c00032 Dengke Li 1
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2023-04-26 , DOI: 10.1021/acs.oprd.3c00032 Dengke Li 1
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The development and optimization of two efficient and convenient routes for the construction of synthetic equivalents of 2-chloro-5-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)aniline, a key intermediate to immuno-oncology agonist (BMS-986299), is described. The developed routes started from commercial available reagents into the desired pyrazole scaffolds smoothly with different substituents such as THP-, Bn-, and PMB-group tolerance. Finally, to further demonstrate the practicability, a large-scale process (10–30 g on a laboratory scale) was obtained through a simple crystallization or filtration without any column chromatography needed and may be suitable for the scalable production of the key intermediate for industrial applications.
中文翻译：
开发制备免疫肿瘤中间体激动剂 BMS-986299 的多功能路线
开发和优化用于构建 2-chloro-5-(1-(tetrahydro-2 H -pyran-2-yl)-1 H -pyrazol-5-yl)aniline合成等价物的两条高效便捷路线，描述了免疫肿瘤激动剂 ( BMS-986299 ) 的关键中间体。开发的路线从市售试剂开始顺利进入所需的吡唑支架，具有不同的取代基，如THP-、Bn-和PMB-群体耐受性。最后，为了进一步证明实用性，通过简单的结晶或过滤获得了大规模工艺（实验室规模为 10-30 g），无需任何柱层析，可能适用于工业关键中间体的规模化生产应用程序。
更新日期：2023-04-26
中文翻译：
开发制备免疫肿瘤中间体激动剂 BMS-986299 的多功能路线
开发和优化用于构建 2-chloro-5-(1-(tetrahydro-2 H -pyran-2-yl)-1 H -pyrazol-5-yl)aniline合成等价物的两条高效便捷路线，描述了免疫肿瘤激动剂 ( BMS-986299 ) 的关键中间体。开发的路线从市售试剂开始顺利进入所需的吡唑支架，具有不同的取代基，如THP-、Bn-和PMB-群体耐受性。最后，为了进一步证明实用性，通过简单的结晶或过滤获得了大规模工艺（实验室规模为 10-30 g），无需任何柱层析，可能适用于工业关键中间体的规模化生产应用程序。
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