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A technology of ceritinib and intermediates, which is applied in the field of preparation of ceritinib, can solve the problems of high cost, low yield, difficult industrialization and the like, and achieves the effects of low cost, simple operation and short synthesis route
Active Publication Date: 2015-02-18
安庆奇创药业有限公司
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[0008] The purpose of the present invention is to overcome the shortcomings of the prior art such as low yield, difficulty in industrialization and high cost, and provide a chemical synthesis method of ceritinib with reasonable process, few steps, simple operation and high reaction yield
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Embodiment 1
[0025] Example 1: Preparation of 2-isopropylmercaptonitrobenzene
[0026] O-Fluoronitrobenzene (10g, 10mmol), add 100ml DMF, add 2-mercaptoisopropanol (5.4g, 70mmol), 25g potassium carbonate, warm to 100 degrees and react for 16h, cool to room temperature, add 500ml water, ethyl acetate (100ml*3) Extract, combine the organic layers, wash with water, wash with saturated brine, dry with anhydrous sodium sulfate, and concentrate to obtain 13.3g of light buttery substance, with a yield greater than 100%, without purification.
Embodiment 2
[0027] Example 2: Preparation of 2-(isopropylsulfonyl)nitrobenzene
[0028] O-Isopropyl mercaptonitrobenzene (13g, 65.97mmol), 120ml of dichloromethane, add m-chloroperoxybenzoic acid (25.67g, 149.42mmol) in batches at room temperature, stir at room temperature for 16h, filter, and concentrate to dryness to obtain a yellowish brown Solid 12g, yield 80%, not purified.
Embodiment 3
[0029] Example 3: Preparation of 2-(isopropylsulfonyl)aniline
[0030] 2-(isopropylsulfonyl)nitrobenzene (2g, 8.73mmol), add 30ml methanol, 0.2g 10% palladium on carbon, hydrogenate at atmospheric pressure for 6h, filter with suction, concentrate and spin off methanol to obtain 1.5g of light butter , The yield is 88%, without purification.
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Abstract
The invention discloses a method for preparing ceritinib, belonging to the field of chemical pharmacy. The method comprises the following steps: by taking 3-bromine-4-methylphenol as an initial raw material, performing phenolic hydroxyl isopropylation, nitration, coupling and reduction reaction, obtaining a midbody 1, by further taking o-nitro fluorobenzene as another initial raw material, performing isosulfhydrylation, oxidation, reduction and pyrimidine, obtaining a midbody 2, performing coupling reduction on the midbody 1 and the midbody 1, obtaining ceritinib which is protected by BOC acid anhydride, and finally removing a t-butyloxycarboryl protecting group, and obtaining ceritinib. The method is simple and feasible to operate, relatively high in yield, small in pollution and applicable to industrial production.
Description
Technical field [0001] The invention belongs to the field of chemical pharmacy, and specifically relates to a preparation method of ceritinib. Background technique [0002] Lung cancer is one of the main causes of cancer death. Non-small cell lung cancer (NSCLC) accounts for 85%-90% of lung cancer cases, and 2%-7% of cases are driven by the rearrangement of the ALK gene, which leads to the accelerated growth of cancer cells. Although the clinical treatment of ALK+NSCLC population has made significant progress, the deterioration of the disease is often inevitable, so more treatment options are needed. Xalkori is an inhibitor of degenerative lymphoma kinase (ALK), which was approved by the FDA in 2011 with accelerated approval and formally approved by the FDA in 2013. It is used in a test kit approved by the FDA to confirm that the tumor is anaplastic lymphoma. Treatment of patients with metastatic non-small cell lung cancer (NSCLC) with positive kinase (ALK). [0003] Xalkori is ...
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