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Method for preparing lenalidomide

A technology of lenalidomide and reflux temperature, applied in the field of lenalidomide and preparation of lenalidomide, can solve the problems of low total yield, long steps, difficult industrialization, etc., and achieves short reaction steps, simple operation, and high reaction high yield effect

Inactive Publication Date: 2015-01-28
SHANGHAI INST OF TECH
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Problems solved by technology

[0010] Aiming at the above-mentioned technical problems in the prior art, the present invention provides a kind of method for preparing lenalidomide, described this method for preparing lenalidomide solves the existing problem of the method for preparing lenalidomide in the prior art The steps are long, the total yield is low, and it is difficult to realize the technical problems of industrialization

Method used

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  • Method for preparing lenalidomide

Examples

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Embodiment 1

[0035] (1) Preparation of 2-methyl-3-nitrobenzoic acid methyl ester

[0036] 30g of 2-methyl-3-nitrobenzoic acid was dissolved in 100mL of anhydrous methanol, and 15mL of thionyl chloride was added dropwise while keeping the temperature below 0°C. After the dropwise addition was completed, it was heated to reflux for 5 hours. Evaporate the methanol and pour it into ice water, adjust the solution to neutral, filter the precipitated solid, wash with distilled water until the filtrate is clear and colorless, and dry the filter cake to obtain 31 g, with a yield of 96%.

[0037] 1 HNMR (500MHz, CDCl 3 )δ: 2.6(s, 3H), 3.95(s, 3H), 7.35(m, 1H), 7.90(m, 2H)

[0038] (2) Preparation of 2-bromomethyl-3-nitrobenzoic acid methyl ester

[0039] Dissolve 20 g of methyl 2-methyl-3-nitrobenzoate in 250 mL of carbon tetrachloride, add 22 g of N-bromosuccinimide (NBS), 2.5 g of benzoyl peroxide (BPO), and heat to 75 The reaction was stirred at °C for 8 hours. After cooling, extract three t...

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Abstract

The invention discloses a method for preparing lenalidomide. The method comprises the following steps: firstly, etherifying 2-methyl-3-nitrobenzoic acid to obtain 2-methyl-3-nitrobenzoic acid methyl ester, brominating to obtain 2-brooethyl-3-nitrobenzoic acid methyl ester, reacting L-glutamine and tert-butyl dicarbonate to obtain N-Boc glutamic acid, acquiring 3-amino-2,6-piperidine diketone protected by Boc from N-Boc-glutamic acid in the presence of a condensing agent and a catalyst, further reacting with acid to prepare 3-amino-2,6-piperidine diketone hydrochloride, reacting 3-amino-2,6-piperidine diketone with 2-brooethyl-3-nitrobenzoic acid methyl ester so as to obtain 3-(4-nitryl-1,3 dihydro-1-oxo-2 hydrogen-isobenzazole-2-yl) piperidine-2,6-diketone, and finally reducing, thereby obtaining lenalidomide. The method disclosed by the invention is high in product yield.

Description

technical field [0001] The invention belongs to the field of organic chemistry, in particular to a kind of lenalidomide, in particular to a method for preparing lenalidomide. Background technique [0002] Lenalidomide is used to treat myelodysplastic syndrome. It is a new immune-modulating, non-chemotherapy anticancer drug. It is an upgraded drug of thalidomide. Influential, it is a new type of immunomodulator developed by Celgene of the United States. It was approved by the FDA in January 2006. Its trade name is Revlimid. It is mainly used for the treatment of myelodysplasia with 5q deletion (the gap gene deletion of the fifth pair of chromosome long arms). syndrome (MDS) subtypes and multiple myeloma (MM). [0003] Myelodysplastic syndrome (MDS) is a clonal hematopoietic neoplasm, a malignant blood disease. When the blood cells in the bone marrow are always in the immature stage and cannot perform their due functions, the myelodysplastic syndrome will occur, making the bo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04
CPCC07D401/04C07C201/12C07C269/04C07D211/88C07C271/12C07C205/58C07C205/57
Inventor 任玉杰鲁加峰陈衍炽
Owner SHANGHAI INST OF TECH
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