Alternative Approach to the Large-Scale Synthesis of the Densely Functionalized Pyrrolidone BMT-415200

Author:

Rakshit Souvik1,Sathasivam Shunmugaraj1,Reddy Raghurami1,Rao Saladi V.1,Shekarappa Vijaykumar1,Kandasamy Moorthy1,Jaleel Mohamed1,Murugan Saravanan1,Bhat Anuradha1,Subramani Tamilarasan1,Lakshminarasimhan Thirumalai1,Gangu Aravind1,Wisniewski Steven R.2ORCID,Kopp Nathaniel2,Hale Ian2,Stevens Jason M.2ORCID,Rosso Victor W.2,Eastgate Martin D.2ORCID,Vaidyanathan Rajappa1ORCID

Affiliation:

1. Chemical Development and API Supply, Biocon Bristol-Myers Squibb Research and Development Center, Biocon Park, Jigani Link Road, Bommasandra IV, Bangalore 560099, India

2. Chemical Process Development, Bristol-Myers Squibb, 1 Squibb Drive, New Brunswick, New Jersey 08903, United States

Publisher

American Chemical Society (ACS)

Subject

Organic Chemistry,Physical and Theoretical Chemistry

Reference34 articles.

1. Lee, K. L.; Allais, C. P.; Dehnhardt, C. M.; Gavrin, L. K.; Han, S.; Hepworth, D.; Lee, A.; Lovering, F. E.; Mathias, J. P.; Owen, D. R.; Papaioannou, N.; Saiah, E.; Strohbach, J. W.; Trzupek, J. D.; Wright, S. W.; Zapf, C. W. Bicyclic-Fused Heteroaryl or Aryl Compounds as IRAK4 Modulators and their Preparation. WO2017033093A1, 2017.

2. Discovery of Clinical Candidate 1-{[(2S,3S,4S)-3-Ethyl-4-fluoro-5-oxopyrrolidin-2-yl]methoxy}-7-methoxyisoquinoline-6-carboxamide (PF-06650833), a Potent, Selective Inhibitor of Interleukin-1 Receptor Associated Kinase 4 (IRAK4), by Fragment-Based Drug Design

3. Anderson, D. R.; Bunnage, M. E.; Curran, K. J.; Dehnhardt, C. M.; Gavrin, L. K.; Goldberg, J. A.; Han, S.; Hepworth, D.; Huang, H.C.; Lee, A.; Lee, K. L.; Lovering, F. E.; Lowe, M. D.; Mathias, J. P.; Papaioannou, N.; Patny, A.; Pierce, B. S.; Saiah, E.; Strohbach, J. W.; Trzupek, J. D.; Vargas, R.; Wang, X.; Wright, S. W.; Zapf, C. W. Bicyclic-Fused Heteroaryl or Aryl Compounds as IRAK4 Inhibitors and their Preparation. WO2015150995A1, 2015.

4. Ahmad, S.; Li, L.; Negash, L. A.; Hynes, J.; Synthesis from Bristol-Myers Squibb Company. Preparation of Thienopyridines and Benzothiophenes as IRAK4 Inhibitors Useful in Treatment and Prevention of Diseases. WO2018/209012 A, 2018.

5. Improvements to Enable the Large Scale Synthesis of 1-{[(2S,3S,4S)-3-Ethyl-4-fluoro-5-oxopyrrolidin-2-yl]methoxy}-7-methoxyisoquinoline-6-carboxamide (PF-06650833)

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