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Method for preparing lenalidomide

A technology of reflux temperature and reaction temperature, applied in the direction of organic chemistry, etc., can solve the problems of long steps, high risk, and difficulty in industrialization, and achieve the effects of low production cost, no three wastes, and short reaction steps.

Active Publication Date: 2010-03-10
SHANGHAI HAOYUAN MEDCHEMEXPRESS CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] In view of this, in order to solve the shortcomings of the existing lenalidomide preparation technology, such as long steps, high risk, and difficulty in realizing industrialization, the prese

Method used

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  • Method for preparing lenalidomide
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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] 18.1g (0.1mol) of 2-methyl-3-nitrobenzoic acid was dissolved in 200ml of anhydrous methanol, and 11.9g (0.1mol) of thionyl chloride was added dropwise at a temperature below 0°C. After the dropping was completed, heat and reflux for 1 hour . Evaporate methanol to dryness, pour into ice water, adjust the pH value to 7-9, stir for 2-3 small test, a yellow solid is precipitated, filtered and dried to obtain 18g of product with a yield of 92.3%.

[0037] 1 H NMR (300MHz, CDCl3) δ: 2.6(s, 3H), 3.95(s, 3H), 7.35(m, 1H), 7.90(m, 2H)

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

[0039] Dissolve 3.9 g (0.02 mol) of methyl 2-methyl-3-nitrobenzoate in 50 ml of chloroform, add 5.3 g (0.04 mol) of NCS (chlorosuccinimide), and heat to reflux for 24 hours. After cooling, add 100ml of water, separate the layers, extract the aqueous phase twice with 20ml of chloroform, combine the c...

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Abstract

The invention discloses a method for preparing lenalidomide (3-(7-amino-3-oxo-1H-isoindole-2-base) piperidine-2,6-diketone). Two intermediates of the lenalidomide are 2-halomethyl-3-nitro-benzoic acidmethyl ester and 3-aminopiperidine-2,6-diketone. The invention discloses methods for preparing the two intermediates and preparing the lenalidomide by using the two intermediates. The method has novel process, short procedures, high reaction yield, low production cost, and larger implementation value and social and economic benefits.

Description

technical field [0001] The invention relates to a chemical synthesis method, in particular to a method for preparing lenalidomide. technical background [0002] Lenalidomide is used in the treatment of myelodysplastic syndrome, and lenalidomide has effects on various biological pathways in cells. At present, celgene is still evaluating the therapeutic effect of this product in hematology and oncology, including multiple myeloma, myelodysplastic syndrome, chronic lymphocytic leukemia and solid tumors. Myelodysplastic syndrome is a hematologic malignancy affecting approximately 300,000 patients worldwide. MDS occurs when blood cells in the bone marrow remain immature and cannot perform their necessary functions. The bone marrow fills with these immature cells, inhibiting the development of normal cells. Patients with myelodysplastic syndrome must often rely on blood transfusions to fight symptoms such as anemia and fatigue until life-threatening iron overload, or iron poiso...

Claims

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Application Information

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IPC IPC(8): C07D401/04
Inventor 高强薛吉军费传增曾亮郑保富
Owner SHANGHAI HAOYUAN MEDCHEMEXPRESS CO LTD
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