Organic Process Research & Development最新文献_第3页

Green Chemistry Articles of Interest to the Pharmaceutical Industry 制药业感兴趣的绿色化学文章

IF 3.1 3区化学

Organic Process Research & Development Pub Date : 2024-09-10 DOI: 10.1021/acs.oprd.4c0030010.1021/acs.oprd.4c00300

Melissa A. Ashley, Miles H. Aukland, Marian C. Bryan*, Megan A. Cismesia, Theresa Dutschei, Oliver D. Engl, Pascal S. Engl, Álvaro Enriquez Garcia, Vanessa Harawa, George Karageorgis, Christopher B. Kelly, Alexandre Leclair, Johnny W. Lee, Zhen Lei, Wei Li, Jan Pawlas, Paul F. Richardson, Samuel C. Scott, Alan Steven*, Balaram S. Takale, Dauzhan Yerkozhanov and Mingshuo Zeng,

引用次数: 0

Unravelling the Impact of Process Impurities on the Crystallization of Ritlecitinib Tosylate Using Molecular Dynamics 利用分子动力学揭示工艺杂质对瑞替西替尼对甲苯磺酸盐结晶的影响

IF 3.4 3区化学

Organic Process Research & Development Pub Date : 2024-09-09 DOI: 10.1021/acs.oprd.4c00106

Clarence KeiKwan Chum, Iain Robert Gladwell, Ivan Marziano, Matteo Salvalaglio

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引用次数: 0

Catalytic Advancements: Optimizing Pd-Based Cross-Coupling Reactions Through Flow Chemistry 催化进展：通过流动化学优化钯基交叉偶联反应

IF 3.4 3区化学

Organic Process Research & Development Pub Date : 2024-09-09 DOI: 10.1021/acs.oprd.4c00027

Iqra S. Patel, Gokul Ganesan, Shilpa Jain

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引用次数: 0

Unravelling the Impact of Process Impurities on the Crystallization of Ritlecitinib Tosylate Using Molecular Dynamics 利用分子动力学揭示工艺杂质对瑞替西替尼对甲苯磺酸盐结晶的影响

IF 3.1 3区化学

Organic Process Research & Development Pub Date : 2024-09-09 DOI: 10.1021/acs.oprd.4c0010610.1021/acs.oprd.4c00106

Clarence KeiKwan Chum, Iain Robert Gladwell, Ivan Marziano* and Matteo Salvalaglio*,

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引用次数: 0

Catalytic Advancements: Optimizing Pd-Based Cross-Coupling Reactions Through Flow Chemistry 催化进展：通过流动化学优化钯基交叉偶联反应

IF 3.1 3区化学

Organic Process Research & Development Pub Date : 2024-09-09 DOI: 10.1021/acs.oprd.4c0002710.1021/acs.oprd.4c00027

Iqra S. Patel, Gokul Ganesan and Shilpa Jain*,

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引用次数: 0

PDI-Functionalized Glass Beads: Efficient, Metal-Free Heterogeneous Photocatalysts Suitable for Flow Photochemistry PDI 功能化玻璃珠：适用于流动光化学的高效、无金属异质光催化剂

IF 3.1 3区化学

Organic Process Research & Development Pub Date : 2024-09-06 DOI: 10.1021/acs.oprd.4c0025610.1021/acs.oprd.4c00256

Hamza Ali, Ifty Ahmed, Karen Robertson* and Anabel E. Lanterna*,

{"title":"PDI-Functionalized Glass Beads: Efficient, Metal-Free Heterogeneous Photocatalysts Suitable for Flow Photochemistry","authors":"Hamza Ali, Ifty Ahmed, Karen Robertson* and Anabel E. Lanterna*, ","doi":"10.1021/acs.oprd.4c0025610.1021/acs.oprd.4c00256","DOIUrl":"https://doi.org/10.1021/acs.oprd.4c00256https://doi.org/10.1021/acs.oprd.4c00256","url":null,"abstract":"Perylene diimides (PDI) have an extraordinary ability to activate both energy and electron transfer processes upon light excitation; however, their extremely low solubility has hindered their wide use as photocatalysts. Here, we show that the combination of solid-supported PDIs with continuous flow photochemistry offers a promising strategy for process intensification and a scalable platform for heterogeneous photocatalysis. The photocatalyst immobilized onto glass beads is highly efficient, easy to separate, and extremely reusable, with a broad synthetic application range. Using the photo-oxidation of n-butyl sulfide as a benchmark reaction, we demonstrate that immobilized PDI are highly active, outperforming reported homogeneous photosensitizers, and capable of extensive reuse (turnover number (TON) >57,000 over 2 months). Transferring the process from batch to flow results in a 10-fold reduction in irradiation time and an increase in the space-time yield by a factor of 33 (40 vs 1338 mmol–1 h–1 L–1 batch vs flow). What is more, the same catalyst sample can be used for the preparation of a range of sulfoxides, the aza-Henry reaction between nitromethane and N–Ar tetrahydroisoquinolines, and the photo-oxidation of furfural with high catalytic activity. Overall, our work combines the remarkable photocatalytic properties of PDI with inert, easy-to-handle glass beads, producing hybrid materials that are reusable and can be adapted for performing heterogeneous photocatalysis in a range of scalable photochemical reactors.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":null,"pages":null},"PeriodicalIF":3.1,"publicationDate":"2024-09-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/acs.oprd.4c00256","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142273820","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

PDI-Functionalized Glass Beads: Efficient, Metal-Free Heterogeneous Photocatalysts Suitable for Flow Photochemistry PDI 功能化玻璃珠：适用于流动光化学的高效、无金属异质光催化剂

IF 3.4 3区化学

Organic Process Research & Development Pub Date : 2024-09-06 DOI: 10.1021/acs.oprd.4c00256

Hamza Ali, Ifty Ahmed, Karen Robertson, Anabel E. Lanterna

{"title":"PDI-Functionalized Glass Beads: Efficient, Metal-Free Heterogeneous Photocatalysts Suitable for Flow Photochemistry","authors":"Hamza Ali, Ifty Ahmed, Karen Robertson, Anabel E. Lanterna","doi":"10.1021/acs.oprd.4c00256","DOIUrl":"https://doi.org/10.1021/acs.oprd.4c00256","url":null,"abstract":"Perylene diimides (PDI) have an extraordinary ability to activate both energy and electron transfer processes upon light excitation; however, their extremely low solubility has hindered their wide use as photocatalysts. Here, we show that the combination of solid-supported PDIs with continuous flow photochemistry offers a promising strategy for process intensification and a scalable platform for heterogeneous photocatalysis. The photocatalyst immobilized onto glass beads is highly efficient, easy to separate, and extremely reusable, with a broad synthetic application range. Using the photo-oxidation of n-butyl sulfide as a benchmark reaction, we demonstrate that immobilized PDI are highly active, outperforming reported homogeneous photosensitizers, and capable of extensive reuse (turnover number (TON) >57,000 over 2 months). Transferring the process from batch to flow results in a 10-fold reduction in irradiation time and an increase in the space-time yield by a factor of 33 (40 vs 1338 mmol–1 h–1 L–1 batch vs flow). What is more, the same catalyst sample can be used for the preparation of a range of sulfoxides, the aza-Henry reaction between nitromethane and N–Ar tetrahydroisoquinolines, and the photo-oxidation of furfural with high catalytic activity. Overall, our work combines the remarkable photocatalytic properties of PDI with inert, easy-to-handle glass beads, producing hybrid materials that are reusable and can be adapted for performing heterogeneous photocatalysis in a range of scalable photochemical reactors.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":null,"pages":null},"PeriodicalIF":3.4,"publicationDate":"2024-09-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142142799","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Development of a Scalable Asymmetric Process for the Synthesis of Selective PDE4B Inhibitor Nerandomilast (BI 1015550) 开发用于合成选择性 PDE4B 抑制剂 Nerandomilast（BI 1015550）的可扩展不对称工艺

IF 3.4 3区化学

Organic Process Research & Development Pub Date : 2024-09-05 DOI: 10.1021/acs.oprd.4c00309

Rogelio P. Frutos, Thomas G. Tampone, Frank Gerstmann, Dirk Weber, Tobias Brodmann, Robert Hagenkötter, Jocelyn Abella, Bing-Shiou Yang, Jason Mulder, Sonia Rodriguez, Heewon Lee, Joe Gao, Jinhua J. Song

引用次数: 0

Development of a Scalable Asymmetric Process for the Synthesis of Selective PDE4B Inhibitor Nerandomilast (BI 1015550) 开发用于合成选择性 PDE4B 抑制剂 Nerandomilast（BI 1015550）的可扩展不对称工艺

IF 3.1 3区化学

Organic Process Research & Development Pub Date : 2024-09-05 DOI: 10.1021/acs.oprd.4c0030910.1021/acs.oprd.4c00309

Rogelio P. Frutos*, Thomas G. Tampone, Frank Gerstmann, Dirk Weber, Tobias Brodmann, Robert Hagenkötter, Jocelyn Abella, Bing-Shiou Yang, Jason Mulder, Sonia Rodriguez, Heewon Lee, Joe Gao and Jinhua J. Song,

{"title":"Development of a Scalable Asymmetric Process for the Synthesis of Selective PDE4B Inhibitor Nerandomilast (BI 1015550)","authors":"Rogelio P. Frutos*, Thomas G. Tampone, Frank Gerstmann, Dirk Weber, Tobias Brodmann, Robert Hagenkötter, Jocelyn Abella, Bing-Shiou Yang, Jason Mulder, Sonia Rodriguez, Heewon Lee, Joe Gao and Jinhua J. Song, ","doi":"10.1021/acs.oprd.4c0030910.1021/acs.oprd.4c00309","DOIUrl":"https://doi.org/10.1021/acs.oprd.4c00309https://doi.org/10.1021/acs.oprd.4c00309","url":null,"abstract":"A robust and scalable synthesis process for Nerandomilast (1, BI 1015550), a selective PDE4B inhibitor with potential therapeutic properties for the treatment of respiratory diseases, was developed and implemented at a pilot plant on a multikilogram scale. Key aspects of the process include the efficient synthesis of intermediate (1-((2-chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-yl)amino)cyclobutyl)methanol (4) by means of a regioselective SNAr reaction between (1-aminocyclobutyl)methanol (6) and 2,4-dichloro-6,7-dihydrothieno[3,2-d]pyrimidine (5), a new convergent synthesis of 5-chloro-2-(piperidin-4-yl)pyrimidine (3) by means of a Suzuki coupling, and a highly enantioselective sulfide oxidation to give chiral nonracemic (R)-2-chloro-4-((1-(hydroxymethyl)cyclobutyl)amino)-6,7-dihydrothieno[3,2-d]pyrimidine 5-oxide (2).","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":null,"pages":null},"PeriodicalIF":3.1,"publicationDate":"2024-09-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142273795","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

One-Step, Catalyst-Free Continuous-Flow Method for the Rapid and Safe Synthesis of 1-Substituted 1H-Tetrazoles 一步法、无催化剂连续流方法快速安全合成 1-取代的 1H 四唑

IF 3.4 3区化学

Organic Process Research & Development Pub Date : 2024-09-05 DOI: 10.1021/acs.oprd.4c00239

Zsolt Fülöp, Péter Bana, Márton Temesvári, Júlia Barabás, Zoltán Kazsu, Zoltán Béni, István Greiner, János Éles

引用次数: 0