Preparation of biomass derived palladium catalyst and application to synthesis of anti-tumor drug osimertinib

An anti-tumor drug, osimertinib technology, applied in the preparation of biomass-derived palladium catalyst, the application field of anti-tumor drug osimertinib synthesis, can solve the difficulty of increasing processing, metal palladium residue, easy blackening of products, etc. problem, to achieve the effect of long service life, easy reaction and low price

Active Publication Date: 2018-06-22
HANGZHOU LUPU BIOTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] In the above method, due to the use of palladium metal, the cost of production is increased, and the product is easy to

Method used

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  • Preparation of biomass derived palladium catalyst and application to synthesis of anti-tumor drug osimertinib
  • Preparation of biomass derived palladium catalyst and application to synthesis of anti-tumor drug osimertinib
  • Preparation of biomass derived palladium catalyst and application to synthesis of anti-tumor drug osimertinib

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Preparation of Biomass-Derived Palladium Catalysts

[0042] In a four-neck flask, add palladium acetate and ethanol solvent, and slowly add chitosan, wherein the molar ratio of palladium acetate to chitosan is 1:1.5; the system is heated to 70°C and reacted for 20 hours. Cool to room temperature, remove ethanol by filtration, rinse the filter cake with ethanol three times, and dry the solid in a vacuum oven at 60°C for 12 hours. The catalyst (Pd(OAc) 2 @Chitosan).

[0043] N-(2-Dimethylamino-ethyl)-2-methoxy-N-methyl-N-[4-(1-methyl-lH-indol-3-yl-pyrimidin-2-yl The preparation method of ]-5-amino-benzene-1,4-diamine, the synthetic route is as follows:

[0044]

[0045] With N-(2-dimethylamino-ethyl-2-methoxy-N-methyl-N-[4-(1-methyl-1H-indol-3-yl-pyrimidin-2-yl ]-5-nitro-benzene-1,4-diamine as raw material, dissolve the above raw material with ethanol, add the catalyst (Pd(OAc) 2 @Chitosan), the molar ratio of the catalyst to the raw material is 0.025:1, the tempe...

Embodiment 2

[0047] Under the catalytic conditions of Example 1, the catalyst was recycled 5 times, and the catalytic effect did not significantly decrease, as shown in Table 1:

[0048] Table 1

[0049] serial number

Embodiment 3

[0051] In four-necked flasks, different palladium salts (a: Pd(OAc) 2 , b: PdCl 2 , c: PdBr 2 , d: Pd(NO 3 ) 2 ), methanol as solvent, chitosan was added slowly, the system was heated up to 60°C, and reacted for 20 hours. Cool to room temperature, remove methanol by filtration, rinse the filter cake with methanol three times, and dry the solid in a vacuum oven at 60°C for 12 hours. The catalyst was obtained by carbonizing at 600°C for 2 hours under the protection of argon, and then elemental analysis was carried out on the catalyst, and it was found that the loading capacity of palladium acetate was the largest, with 9.8%, and palladium chloride, palladium bromide, and palladium nitrate were 9.6%, respectively. 9.5%, 8.5%, and then verify the reaction of the four catalysts, consistent with the experimental results, the greater the metal loading, the better the catalyst activity, respectively 97, 96, 96, 93, so the preferred catalyst is palladium acetate . Afterwards, the...

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Abstract

The invention relates to a preparation method of a biomass derived palladium catalyst and application to synthesis of an anti-tumor drug osimertinib. The preparation method comprises the following process: enabling chitosan and palladium salt to react in the presence of a solvent to form a complex; then cooling to room temperature; drying a solid in vacuum to remove a solvent; under the protectionof argon gas, carbonizing at high temperature to obtain the catalyst; dissolving a raw material N-(2-dimethylamino-ethyl-2-methoxy-N-methyl-N-[4-(1-methyl-1H-indole-3-yl-pyrimidine-2-yl)-5-nitryl-benzene-1,4-diamine and adding the catalyst; stirring at temperature of 0 to 120 DEG C for 5 to 12h; dropwise adding hydrazine hydrate; after completely reacting, cooling to room temperature and filtering; spinning and drying the solvent to obtain a faint yellow solid. The preparation method provided by the invention has the advantages of wide raw material source, relatively low price, moderate reaction conditions and high yield; the catalyst has high activity, high stability, high dispersity of active components and long service life; the catalyst can be repeatedly used for a plurality of timesand the preparation method also has the advantages of short flow, easiness for controlling reaction and simple equipment requirements; complicated post-treatment is avoided and environment pollution is avoided.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis and the preparation of raw materials, and in particular relates to a preparation method of a biomass-derived palladium catalyst and its application in the synthesis of an antitumor drug osimertinib. Background technique [0002] Osimertinib, the English name Osimertinib, was developed by AstraZeneca in the United Kingdom. Due to the treatment of advanced non-small cell lung cancer patients with epidermal growth factor receptor (EGFR) T790M mutation or resistance to other EGFR inhibitors, the US FDA approved it in November 2015. It was approved for marketing in January, because Tagrisso is an irreversible inhibitor of EGFR, which can form a covalent bond with the molecular target, so theoretically the response lasts for a long time, and the chance of developing drug resistance is relatively reduced. If Tagrisso can finally be approved as a first-line drug for EGFR-mutant non-small cell lu...

Claims

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Application Information

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IPC IPC(8): B01J23/44B01J37/03B01J37/08C07D403/04
CPCB01J23/44B01J37/03B01J37/084B01J37/086C07D403/04
Inventor 沈鸿云沈超冯冬祥
Owner HANGZHOU LUPU BIOTECH CO LTD
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