Amgen Inc.

Matthew G Beaver

Sheng Cui

Liang Huang

Jason S Tedrow

Neil Fred Langille

Andrew Thomas Parsons

Robert Ronald Milburn

Philipp C Roosen

Austin G Smith

Alan H Cherney

Xianqing Shi

Oliver Thiel

John T Colyer

Ari Ericson

Simone Spada

Carolyn Cohen

Kyle D Baucom

Gabrielle St-pierre

Rahul P Sangodkar

Michael A Lovette

The present disclosure relates to an improved, efficient, scalable process to prepare intermediate compounds, such as 2,2′,2″-(1,3,5,2,4,6-trioxatriborinane-2,4,6-triyl)tris(3-fluorophenol), useful for the synthesis of compounds, such as Compound 9, for the treatment of KRAS G12C mutated cancers.

Synthesis of KRAS G12C inhibitor compound

Provided herein are processes for synthesizing Mcl-1 inhibitors and intermediates such as compound F that can be used to prepare them where the variable PG is as defined herein. In particular, provided herein are processes for synthesizing compound A1, and salts or solvates thereof and compound A2, and salts and solvates thereof.

Ring closing synthesis of macrocyclic MCL-1 inhibitor intermediates

Provided herein are processes for synthesizing apremilast comprising reacting 3-acetamidophthalic anhydride and (S)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethan-1-amine or a salt thereof to form apremilast. Also provided are processes for isolating apremilast from the reaction mixture, as described herein.

Process for synthesizing apremilast

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Natick, MA, United States of America

Matthew G Beaver