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Method for preparing prucalopride impurity

A technology of impurity and reaction, applied in the field of preparing prucalopride impurity, can solve the problem of high price of boron tribromide

Inactive Publication Date: 2014-04-16
万全万特制药江苏有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In literature reports, boron tribromide is often used as a chemical reagent for removing methoxy groups, but boron tribromide is expensive

Method used

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  • Method for preparing prucalopride impurity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] Add 5.0 g of N-[1-(3-methoxypropyl)]-4-amino-5-chloro-2,3-dihydrobenzofuran-7-carboxamide into a 100 mL three-necked flask, and add 50 mL Hydrobromic acid (40%), heat up to 85°C to react, TLC detects the reaction, after the reaction is completed, cool down to room temperature, adjust the reaction solution to neutral with sodium hydroxide solution, filter the resulting solid, and dichloromethane and methanol recrystallized, N-[1-(3-hydroxypropyl)]-4-amino-5-chloro-2,3-dihydrobenzofuran-7-carboxamide, the yield was 75%.

Embodiment 2

[0015] Add 5.0 g of N-[1-(3-methoxypropyl)]-4-amino-5-chloro-2,3-dihydrobenzofuran-7-carboxamide into a 100 mL three-necked flask, add 30 mL Hydrobromic acid (40%), heat up to 70°C to react, TLC to detect the reaction, after the reaction is completed, cool down to room temperature, adjust the reaction solution to neutral with sodium hydroxide solution, filter the resulting solid, and dichloromethane and methanol recrystallized, N-[1-(3-hydroxypropyl)]-4-amino-5-chloro-2,3-dihydrobenzofuran-7-carboxamide, the yield was 55%.

Embodiment 3

[0017] Add 5.0 g of N-[1-(3-methoxypropyl)]-4-amino-5-chloro-2,3-dihydrobenzofuran-7-carboxamide into a 100 mL three-necked flask, add 30 mL Hydrobromic acid (40%), heat up to 100°C to react, TLC to detect the reaction, after the reaction is completed, cool down to room temperature, adjust the reaction solution to neutral with sodium hydroxide solution, filter the resulting solid, and dichloromethane and methanol recrystallized, N-[1-(3-hydroxypropyl)]-4-amino-5-chloro-2,3-dihydrobenzofuran-7-carboxamide, the yield was 70%.

[0018]

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PUM

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Abstract

The invention belongs to the field of medicinal chemistry and relates to a method for preparing a prucalopride impurity. The method comprises the following steps: reacting N-[1-(3-methoxypropyl)]-4-amino-5-chloro-2,3-dihydrobenzofuran-7-formamide and a demethoxy reagent so as to obtain the prucalopride impurity N-[1-(3-hydroxypropyl)]-4-amino-5-chloro-2,3-dihydrobenzofuran-7-formamide. The adopted reagent is economic and readily available, the synthetic method is simple and convenient in operation, and the reaction conditions are mild.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry and relates to a method for preparing prucalopride impurities. Background technique [0002] EP-0,445,862-A published on September 11, 1991 discloses N-(4-piperidinyl)(dihydrobenzofuran or dihydro-2H-benzopyridine) having the property of stimulating gastrointestinal motility furan) formamide derivatives. [0003] WO-96 / 16060 published on May 30, 1996 specifically discloses the compound 4-amino-5-chloro-2,3-dihydro-N-[1-(3-methoxypropyl)-4-piper Pyridyl]-7-benzofurancarboxamide, which is commonly known as "Prucalopride". Prucalopride promotes cholinergic and non-cholinergic non-adrenergic excitatory neurotransmission in animals and stimulates colonic motility and defecation. It acts on 5-HT 2A and 5-HT 3A Receptor has no affinity, however, is 5-HT 4 Potent selective agonist of the receptor. Prucalopride induces massive contractions of the colon, which propagate in the form of peristaltic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/12
CPCC07D405/12
Inventor 刘亚男闫起强马苏峰
Owner 万全万特制药江苏有限公司
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