TRAVIS P. REMARCHUK, PH.D. Office: (650) 467-8834 Email: travisr@gene.com Work Experience 05/15-Present Senior Scientist, Small Molecule Process Chemistry, Genentech (A Member of the Roche Group), South San Francisco, CA. 2006–2015 Scientist, Small Molecule Process Chemistry, Genentech (A Member of the Roche Group), South San Francisco, CA. 1995–1998 Research Associate, Process Chemistry, Agouron Pharmaceuticals, Inc. San Diego, CA. 1994-1995 Research Associate, Medicinal Chemistry, La Jolla Pharmaceuticals, Inc., San Diego, CA. Education 2003–2006 1998-2003 1989-1994: Postdoctoral Studies, Harvard University, Department of Chemistry and Chemical Biology, Cambridge, MA. Advisor: Professor E. J. Corey (Nobel Laureate). Ph.D. Organic Chemistry, University of California, Irvine, Irvine, CA. Advisor: Professor Larry E. Overman, Distinguished Professor of Chemistry. B.Sc. in Chemistry, University of Saskatchewan, Saskatoon, SK, Canada. Advisor: Professor M. Majewski. Publications 1. Dong, M. W.; Al-Sayah, M.; Goel, M.; Remarchuk, T. “HPLC Method Development Strategies for Small Molecule Drug Candidates with Multiple Chiral Centers: A Case Study” J. Biomed. Pharm. Anal. 2015. Manuscript Submitted. 2. Featured in Pharmaceutical Technology article titled: “Practical Approaches to Large-Scale Heterocyclic Synthesis” December 1st, 2014 (Interview by Cynthia Challener). 3. Remarchuk, T. St-Jean, F.; Carrera, D.; Savage, S.; Yajima, H.; Wong, B.; Babu, S.; Deese, A.; Stults, J.; Dong, M. W.; Askin, D.; Lane, J. W.; Spencer, K. L. "Synthesis of Akt Inhibitor Ipatasertib. Part 2. Total Synthesis and First Kilogram Scale-up" Org. Process Res. Dev. 2014, 18, 1652–1666. 4. Lane, J. W.; Spencer, K. L.; Shakya, S. R.; Kallan, N. C.; Stengel, P. J.; Remarchuk, T. "Synthesis of Akt Inhibitor Ipatasertib. Part 1. Route Scouting and Early Process Development of a Challenging Cyclopentylpyrimidine Intermediate" Org. Process Res. Dev. 2014, 18, 1641–1651. 5. Remarchuk, T. P.; Babu, S.; Stults, J.; Zanotti-Gerosa, A.; Roseblade, S.; Yang, S.; Huang, P.; Sha, C.; Wang, Y. “An Efficient Catalytic Asymmetric Synthesis of a 2-Amino Acid on MultiKilogram Scale” Org. Process Res. Dev. 2014, 18, 135–141. Highlighted in Synfacts, 2014. 6. Wigman, L.; Remarchuk, T.; Gomez, S. R.; Kumar, A.; Dong, M. W.; Medley, C. D.; Chetwyn, N. P. “Byproducts of Commonly Used Coupling Reagents: Origin, Toxicological Evaluation and Methods for Determination” Am. Pharm. Rev. (2014). 7. Lou, Y.; Remarchuk, T. P.; Corey, E. J. "Catalysis of Enantioselective [2+1]-Cycloaddition Reactions of Ethyl Diazoacetate and Terminal Acetylenes Using Mixed-Ligand Complexes of the Series Rh2(RCO2)n(L*4–n). Stereochemical Heuristics for Ligand Exchange and Catalyst Synthesis" J. Am. Chem. Soc. 2005, 127, 14223–14230 8. Overman, L. E.; Remarchuk, T. "Catalytic Asymmetric Intramolecular Aminopalladation: Enantioselective Synthesis of Vinyl-Substituted 2-Oxazolidinones, 2-Imidazolidinones and 2Pyrrolidinones" J. Am. Chem. Soc. 2002, 124, 12–13 1 TRAVIS P. REMARCHUK, PH.D. 9. Albizati, K. F.; Babu, S.; Birchler, A.; Busse, J. K.; Fugett, M.; Grubbs, A.; Haddach, A.; Pagan, M.; Potts, B.; Remarchuk, T.; Rieger, D.; Rodriguez, R.; Shanley, J.; Tibbetts, T.; Whitten, K.; Borer, B. C. "A Synthesis of the HIV-Protease Inhibitor Nelfinavir from D-Tartaric Acid" Tet. Lett. 2001, 42, 6481–6485 Patents 1. Angelaud, R.; Beaudry, D. R.; Carrera, D. E.; Malhotra, S.; Remarchuk, T.; St-Jean, F. “Process for Making Benzoxazepin Compounds” Application# 14/205,634; Docket# P4974R1 (2014) 2. Remarchuk, T., Process for Making Amino Acid Compounds. PCT/US13/41687/2012 3. Askin, D.; Han, C.; Lane, J.; Remarchuk, T. P.; Shakya, S.; Sowell, G.; Spencer, K. L.; Stengel, P. J. "Process for Making Hydroxylated Cyclopentylpyrimidine Compounds" PCT/US13/41666/2012 4. Babu, S.; Gosselin, F.; Ran, Y.; Remarchuk, T.; Savage, S.; Stults, J.; Yajima, H. "Process of Making Hydroxylated Cyclopentylpyrimidine Compounds and Salts" PCT/US2013/041695 5. Lane, J.; Remarchuk, T.; Shakya, S.; Spencer, K.; Stengel, P. "Process for Making Hydroxylated Cyclopentylpyrimidine Compounds" PCT/US13/41624/2012 6. Babu, S.; Borer, B. C.; Remarchuk, T. P.; Szendroi, R. J.; Whitten, K. R.; Busse, J. K.; Albizati, K. F. "Methods of Making Intermediates for the Preparation of the HIV Protease Inhibitor Nelfinavir" US/1999/5925759 7. Babu, S.; Borer, B. C.; Remarchuk, T. P.; Szendroi, R. J.; Whitten, K. R.; Busse, J. K.; Albizati, K. F. "Preparation of Intermediates for the HIV-Protease Inhibitor Nelfinavir" US/1998/5705647 8. Tao, J.; Babu, S.; Dagnino, R., Jr.; Tian, Q.; Remarchuk, T. P.; McGee, K. S.; Nayyar, N. K.; Moran, T. J. "Process for Preparation of Amidopentenoate Peptide Analog Rhinovirus Protease Inhibitors" US/2001/99-150365 9. Tian, Q.; Nayyar, N., K.; Babu, S.; Tao, J.; Moran, T. J.; Dagnino, R., Jr.; Mitchell, L. J.; Remarchuk, T. P.; Melnick, M. J.; Bender, S. L. "Synthetic Routes for the Preparation of Rhinovirus Protease Inhibitors and Key Intermediates" US/2001/99-150368 Invited Presentations Sept 2014 Aug 2014 June 2014 Sept 2013 July 2013 July 2012 Sabbatical lectures: “Process Development of PI3k -Sparing Inhibitor GDC-0032 (Taselisib)” (1) RIKEN, JP; (2) Chugai, JP; (3) LG Company, SK; (4) Korea Advanced Institute of Science and Technology (KAIST), Daejeon, SK; (5) Busan National University, Busan, SK; (6) Sungkyunkwan University (SKKU), Suwon, SK 248th ACS National Meeting August 10–14th. Presentation: Remarchuk, T. P. "Part II. Development of a Manufacturing Route to PI3k -Sparing Inhibitor GDC-0032 (Taselisib)" San Francisco, CA GRC, Heterocycles. Presentation: Remarchuk, T. P. "Process Route Development of PI3kSparing inhibitor GDC-0032 (Taselisib)" 246th ACS National Meeting & Symposium; Presentation: Remarchuk, T. P. "Route Selection and Early Stage Process Development of AKT Inhibitor GDC-0068" Indianapolis, IN NORM ‘13 Conference; Presentation: Remarchuk, T. P. "Route Selection and Early Stage Process Development of AKT Inhibitor GDC-0068" Corvallis, OR GRC, Organic Reactions and Processes. Presentation: Remarchuk, T. P. "Process Development Toward a Manufacturing Route for the AKT Inhibitor GDC-0068" 2 TRAVIS P. REMARCHUK, PH.D. April 2012 Sept 2012 June 2011 May 2011 May 2011 May 2011 May 2008 Sept 2006 July 1998 Mar 1994 14th Annual MINT (Meeting on Innovation and New Technology) Conference at Roche Basel, Switzerland. Presentation: Remarchuk, T. P. & Savage, S. "gRED Small Molecule Process Chemistry Innovation on GDC-0068 (RG7440)" Asilomar Research Conference. Poster: "Acceleration of PI3K Beta-Sparing Inhibitor GDC0032 to Ph III “Speed to Discovery, Development and to Patients”" St. Jean, F., Angelaud, R.; Askin, D. & Remarchuk, T. Genentech Small Molecule Drug Discovery (SMDD) Offsite Meeting, South San Francisco convention center. Presentation: Remarchuk, T. P. "Process Chemistry Development of AKT Inhibitor GDC-0068" Asilomar Research Conference. Poster: "Process Chemistry on the AKT Inhibitor GDC0068: Enabling Uninterrupted Clinical Supply" Han, C.; Gosselin, F.; Remarchuk, T.; Carrera, D.; Savage, S.; Yajima, H.; & St. Jean, F. Asilomar Conference: "Process Development and GMP Manufacturing of the PI3K BetaSparing Inhibitor GDC-0032" St-Jean, F.;* Wong, B.; Remarchuk, T.; & Askin, D. Asilomar Research Conference. Poster: "Quality challenges of AKT inhibitor GDC-0068 API resupply campaigns: Transitioning complex candidates to clinic" Dong, M. W.; Yazzie, D. T.; Remarchuk, T.; Chetwyn, N. P. Asilomar Research Conference. Poster: "Scale-Up Strategy for Small Molecule APIs at Genentech" Rogers, R.; Wong, B.; Yajima, H.; Savage, S.; Babu, S. and Remarchuk, T.* Asilomar Research Conference. Poster: "Scale-Up Strategy for Small Molecule APIs at Genentech" Remarchuk, T. P.;* Ha, E.;* Savage, S.; Yajima, H.; Cheng, K.; Tian, Q.; Stumpf, A.; Babu, S. & Reynolds, M. GRC, Organic Reactions and Processes, Henniker, NH Poster: Remarchuk, T. P. "Recent Developments Towards the Synthesis of HIV Protease Inhibitor Viracept® From D-(–)-Tartaric Acid" Western Undergraduate Conference, Lethbridge, AB, Canada. Poster: Remarchuk, T. P.; Lazny, R.; Majewski, M. "Synthesis of Chiral Amines as Reagents for Enantioselective Deprotonations in the Asymmetric Synthesis of Tropane Alkaloids" Conferences Attended July 2014 July 2011 July 2010 July 2009 July 2008 July 2007 Aug 1997 July 1996 Oct 1995 Gordon Research Conference Organic Reactions and Processes, RI Gordon Research Conference; Organic Reactions and Processes, RI Baltic Organic Symposium (BOS) in organic chemistry; Riga, Latvia Gordon Research Conference; Organic Reactions and Processes, RI Gordon Research Conference; Organic Reactions and Processes, RI Gordon Research Conference; Organic Reactions and Processes, RI Gordon Research Conference; Organic Reactions and Processes, Henniker, NH Gordon Research Conference; Organic Reactions and Processes, New Hampton School, NH The 10th Annual William S. Johnson Symposium in Organic Chemistry, Stanford University 3