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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, difficult industrialization, high risk, etc., and achieve the effect of low production cost, short reaction steps, and no three wastes

Active Publication Date: 2012-11-21
SHANGHAI HAOYUAN MEDCHEMEXPRESS CO LTD
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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 present invention provides a new preparation method, which has simple and convenient process, cheap and easy-to-obtain raw materials, and high yield. High, high safety, suitable for industrial production

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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 methyl 2-methyl-3-nitrobenzoate

[0036] 18.1g (0.1mol) of 2-methyl-3-nitrobenzoic acid, dissolved in 200ml of anhydrous methanol, keep below 0℃, add 11.9g (0.1mol) of thionyl chloride dropwise, after dripping, heat to reflux for 1 hour . The methanol was evaporated to dryness, poured into ice water, the pH was adjusted to 7-9, stirred for 2-3 small tests, a yellow solid was precipitated, filtered, and dried to obtain 18 g 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 methyl 2-chloromethyl-3-nitrobenzoate

[0039] 3.9 g (0.02 mol) of methyl 2-methyl-3-nitrobenzoate was dissolved in 50 ml of chloroform, 5.3 g (0.04 mol) of NCS (chlorosuccinimide) was added, and the mixture was heated to reflux for 24 hours. After cooling, 100ml of water was added for liquid separation, the aqueous phase was extracted twice with 20ml of chloroform, combined with chlorofor...

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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 acid methyl 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 (lenalidomide) is used to treat myelodysplastic syndromes. Lenalidomide has effects on many biological pathways in cells. At present, celgene is still evaluating the therapeutic effects of this product in hematology and oncology, including multiple myeloma, myelodysplastic syndrome, chronic lymphocytic leukemia and solid tumors. Myelodysplastic syndrome is a malignant hematological disease with approximately 300,000 patients worldwide. When the blood cells in the bone marrow are always in the immature stage and cannot perform their necessary functions, myelodysplastic syndrome occurs. The bone marrow is full of these immature cells, inhibiting the development of normal cells. Patients with myelodysplastic syndromes must often rely on blood transfusions to combat symptoms such as anemia and fatigue, until t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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