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ChemicalBook CAS DataBase List Cabozantinib Malate
1140909-48-3

Cabozantinib Malate synthesis

10synthesis methods
Of the three syntheses of cabozantinib reported, the kilo-gram scale process route is described in the scheme.


The preparation began with 6,7-dimethoxy-quinoline-4-ol (46) which upon treatment with POCl3 provided chloride 47 in 70% yield. Exposure of 47 to 4-aminophenol under basic conditions using t- BuONa furnished diaryl ether 48 in 72% yield. This aniline was then coupled with amidoacid chloride 51 (which arose from the activation of commercial diacid 49 to the corresponding monochloride and coupling with p-fluoroaniline and subsequent exposure to oxalyl chloride to furnish the transient acid chloride) to construct cabozantinib as the free base 52 in 95% yield. Salt formation of cabozantinib 52 was carried out with (S)-malic acid, which ultimately delivered the final product of cabozantinib (S)- malate (VIII) in 75% yield.
849217-68-1 Synthesis
Cabozantinib

849217-68-1
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Cabozantinib Malate

1140909-48-3
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Yield:1140909-48-3 92.26%

Reaction Conditions:

in tetrahydrofuran at 50 - 70;Large scale;Solvent;

Steps:

3; 6 Example 6: Synthesis of Cabozantinib Malate

Add 800.0g of cabozantinib to 12.0L of tetrahydrofuran and raise the temperature to 5070,Add 264.7g of L-malic acid solid directly, continue to stir for 23h, cool to 1020, stir for 12h, filter, rinse with 1.6L tetrahydrofuran,The filter cake was vacuum dried at 50±5°C to a constant weight to obtain 935.4 g of cabozantinib malate.The HPLC purity is 99.91%, the yield is 92.26%, and the maximum single impurity is 0.02% (see Figure 6 for the HPLC chart).

References:

CN112979544,2021,A Location in patent:Paragraph 0042-0044; 0049-0050

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