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Method for producing lesinurad intermediate 4-cyclopropyl-1-naphthylamine

A compound and molar technology, applied in the field of medicine, can solve problems such as unsatisfactory safety and economy

Inactive Publication Date: 2016-06-01
TIANJIN INSTITUTE OF PHARMA RESEARCH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The present invention is to solve the shortcomings of the prior art (that is, the problem that compound 1 is accompanied by a large amount of by-product 3 in the process of catalytic hydrogenation reduction to prepare 2, and the safety and economy are not ideal), and provides a method to avoid the use of The preparation process of hydrogen and noble metal catalyst without producing by-products 3, the process has the characteristics of high product purity, good safety and low cost

Method used

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  • Method for producing lesinurad intermediate 4-cyclopropyl-1-naphthylamine
  • Method for producing lesinurad intermediate 4-cyclopropyl-1-naphthylamine
  • Method for producing lesinurad intermediate 4-cyclopropyl-1-naphthylamine

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] 21.32g (0.1mol) of 4-cyclopropyl-1-nitronaphthalene 1 was dissolved in 300mL of absolute ethanol, stirred at room temperature, 7.68g of 10% Pd / C was added, and catalytic hydrogenation was carried out overnight at room temperature, TLC showed that the reaction was complete .

[0015] The reaction mixture was suction filtered to remove the catalyst, the filtrate was evaporated on a rotary evaporator to remove the solvent, and the obtained residue was purified by column chromatography to obtain product 2, a light red oily liquid, 13.56 g, with a yield of 74%. 1 HNMR (DMSO-d 6 ,400MHz),δ:8.24(d,1H,J=8.4Hz),8.07(d,1H,J=8.4Hz),7.46-7.50(m,1H),7.37-7.41(m,1H),6.99( d,1H,J=7.6Hz),6.59(d,1H,J=8.0Hz),5.52(bs,2H),2.10-2.15(m,1H),0.89-0.93(m,2H),0.53-0.57 (m,2H).

[0016] go through 1 According to HNMR analysis, the compound 2 prepared above contains a certain amount of by-product 3 (see summary in Table 1).

Embodiment 2

[0018] 21.32g (0.1mol) of 4-cyclopropyl-1-nitronaphthalene 1 was dissolved in 1000mL of absolute ethanol, stirred at room temperature, 7.68g of 10% Pd / C was added, and catalytic hydrogenation was carried out overnight at room temperature, TLC showed that the reaction was complete .

[0019] The reaction mixture was suction filtered to remove the catalyst, the filtrate was evaporated to remove the solvent on a rotary evaporator, and the obtained residue was purified by column chromatography to obtain product 2, a light red oily liquid, 13.38 g, with a yield of 73%.

[0020] go through 1 According to HNMR analysis, the compound 2 prepared above contains a certain amount of by-product 3.

Embodiment 3

[0022] 21.32g (0.1mol) of 4-cyclopropyl-1-nitronaphthalene 1 was dissolved in 200mL of absolute ethanol, stirred at room temperature, 1.07g of 10% Pd / C was added, and catalytic hydrogenation was carried out overnight at room temperature, TLC showed that the reaction was complete .

[0023] The reaction mixture was suction filtered to remove the catalyst, the filtrate was evaporated to remove the solvent on a rotary evaporator, and the obtained residue was purified by column chromatography to obtain product 2, a light red oily liquid, 13.01 g, with a yield of 71%.

[0024] go through 1 According to HNMR analysis, the compound 2 prepared above contains a certain amount of by-product 3.

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Abstract

The invention discloses a synthetic method which can be applied to produce gout treating drug lesinurad intermediate 4-cyclopropyl-1-naphthylamine 2. The method adopts metal or low-price salt as a reducing agent, to provide a production technique which can avoid the application of hydrogen and precious metal catalysts without producing a by-product 3. The present technique has the characteristics of high purity products, good security and low cost.

Description

technical field [0001] The invention belongs to the technical field of medicine, specifically relates to the field of preparation technology of pharmaceutical intermediates, and more specifically relates to a synthetic method which can be used to prepare 4-cyclopropyl-1-naphthylamine, an intermediate of URAT1 inhibitor lesinurad, a drug for treating gout. Background technique [0002] Gout is a chronic metabolic disease characterized by hyperuricemia and pain caused by deposition of monosodium uric acid (MSU) in joints and other parts. The main reason is purine metabolism disorder and / or uric acid excretion disorder. There are tens of millions of gout patients worldwide. Lesinurad (RDEA594) is an oral drug developed by Ardea that can inhibit the uric acid transporter (uratetransporter1, URAT1) in the kidney and excrete uric acid in the blood. It was first developed from Valeant's antiviral drug RDEA806 (as shown in the following formula) . Now the ownership of lesinurad be...

Claims

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Application Information

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IPC IPC(8): C07C209/36C07C211/60
Inventor 赵桂龙田禾蔡文卿刘钰强谢亚非徐为人汤立达邹美香
Owner TIANJIN INSTITUTE OF PHARMA RESEARCH
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