ChemicalBook CAS DataBase List Cabozantinib

Cabozantinib synthesis

4synthesis methods

Product Name:Cabozantinib
CAS Number:849217-68-1
Molecular formula:C28H24FN3O5
Molecular Weight:501.51

Cabozantinib, also known as XL-184 or BMS-907351, is an orally bioavailable, small molecule receptor tyrosine kinase (RTK) inhibitor with potential antineoplastic activity. Cabozantinib strongly binds to and inhibits several tyrosine receptor kinases. Specifically, cabozantinib appears to have a strong affinity for the hepatocyte growth factor receptor (Met) and vascular endothelial growth factor receptor 2 (VEGFR2), which may result in inhibition of tumor growth and angiogenesis, and tumor regression. Cabozantinib was approved by the U.S. FDA in November 2012 for the treatment of medullary thyroid cancer.

Synthetic Routes

ROUTE 1

ROUTE 2

ROUTE 3

ROUTE 4

ROUTE 5

ROUTE 6

Laus, Gerhard; Schreiner, Erwin; Nerdinger, Sven; Kahlenberg, Volker; Wurst, Klaus; Vergeiner, Stefan; Schottenberger, Herwig. Crystal structures of intermediates in a new synthesis of antitumor drug cabozantinib. Heterocycles. Volume 93. Issue 1, Spec. Issue. Pages 323-332. Journal; Online Computer File. (2016).

1140909-48-3 Synthesis

1140909-48-3
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849217-68-1
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Yield:849217-68-1 100%

Reaction Conditions:

with sodium hydrogencarbonate in water;ethyl acetate at 45; for 2 h;

Steps:

41 Example 41

A cabozantinib monolauryl sulfate salt was prepared by the following general procedure: a. 37 g of cabozantinib S-malate was added to a co-solvent of (1850 mL/740 mL) of ethyl acetate/l0% aqueous NaHC0₃ (50V/20V) and stirred at 45°C for 2 hour; (0518) b. The organic layer of the reaction mixture of step (a) was separated and washed twice with 740 mL of purified water (20V x 2); (0519) c. The organic extracts of step (b) were combined and concentrated to obtain cabozantinib free base as a white powder (29.2 g, 100% yield)

References:

WO2019/241504,2019,A1 Location in patent:Page/Page column 110

190728-25-7 Synthesis