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Wednesday, 27 March 2019


Taselisib skeletal.svg



Manufacture of the PI3K β-Sparing Inhibitor Taselisib. Part 2: Development of a Highly Efficient and Regioselective Late-Stage Process

 Department of Small Molecule Process ChemistryGenentech Inc.1 DNA Way, South San Francisco, California 94080, United States
 Small Molecules Technical Development PTDC-CF. Hoffmann-La Roche Ltd.Grenzacherstrasse 124, 4070 Basel, Switzerland
Org. Process Res. Dev., Article ASAP
DOI: 10.1021/acs.oprd.9b00050
*E-mail: stjean.frederic@gene.com. (F.St.-J.), *E-mail: angelaud.remy@gene.com. (R.A.)
Abstract Image
A highly efficient and regioselective manufacturing route for the phosphoinositide 3-kinase β-sparing inhibitor taselisib was developed. Highlights of the synthesis include: (1) magnesium-mediated formation of a challenging cyclic amidine; (2) regioselective imidazole construction via alkylation/condensation with bromopyruvic acid; and (3) triazole formation with 2-isopropyl acetamidrazone to generate the key bromobenzoxazepine core intermediate. Subsequent highly efficient one-pot palladium-catalyzed Miyaura borylation/Suzuki cross-coupling/saponification, followed by a 1,1′-carbonyldiimidazole-mediated coupling with ammonia, led to the pentacyclic taselisib. This new synthetic approach provides a more efficient route to taselisib with a significant decrease in process mass intensity compared to the previous early development routes to the bromobenzoxazepine core. Finally, implementation of a controlled crystallization provided the active pharmaceutical ingredient with the desired polymorphic form.
Taselisib was obtained in 90% yield (16.2 kg) as a white to off-white solid (>99.9 wt %; >99.9 A%) as Form B crystal.
mp (DSC): 257–258 °C.
HRMS (ESI-CID) m/z Calcd for [M + H]+ C24H29N8O2: 461.2408; found: 461.2409.
 1H NMR (600 MHz, DMSO-d6) δ ppm 8.41 (s, 1H), 8.37 (d, J = 8.4, 1H), 8.02 (s, 1H), 7.88 (m, 1H), 7.45 (dd, J = 8.4, 1.7 Hz, 1H), 7.36 (d, J = 1.7 Hz, 1H), 7.20 (br s, 1H), 6.84 (br s, 1 H), 5.83 (sept, J = 6.6 Hz, 1H), 4.53–4.51 (m, 2H), 4.52 (m, 2H), 2.26 (s, 3H), 1.75 (s, 6H), 1.47 (d, J = 6.7 Hz, 6H).
 13C NMR (DMSO-d6, 151 MHz) δ = 173.8, 158.3, 155.9, 147.3, 144.0, 136.6, 134.6, 130.3, 129.9, 126.4, 123.6, 120.4, 119.3, 116.2, 115.3, 68.3, 64.5, 49.9, 49.7, 25.5, 25.5, 22.3, 22.3, 13.8.
Ultraviolet/Visible Spectroscopy
Apparatus: Perkin Elmer, UV-6190, Lambda 25
Solvent: Acetonitrile/Water 1:1 (v/v)

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