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Synthesis method of 6-(4-methylpiperazine-1-yl)-4-o-tolyl nicotinamide

A technology of phenylnicotinamide and a synthesis method, applied in directions such as organic chemistry, can solve problems such as complicated steps and increased cost, and achieve the effects of fewer steps in a reaction process, mild reaction conditions, and safety and environmental protection in the reaction process

Pending Publication Date: 2022-03-15
ZHEJIANG UNIV OF TECH
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

3 to 5 molar equivalents of o-tolylmagnesium chloride are needed for the addition reaction between the raw material and the Grignard reagent, and 5 molar equivalents of glacial acetic acid are added when DDQ is used for oxidation, and all of it needs to be neutralized in the post-treatment. and, undoubtedly, a substantial increase in cost
Unnecessary solvents are added in the synthesis, the steps are cumbersome and the cost increases

Method used

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  • Synthesis method of 6-(4-methylpiperazine-1-yl)-4-o-tolyl nicotinamide
  • Synthesis method of 6-(4-methylpiperazine-1-yl)-4-o-tolyl nicotinamide
  • Synthesis method of 6-(4-methylpiperazine-1-yl)-4-o-tolyl nicotinamide

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Embodiment 1

[0037] Step (1) Synthesis of 4-orthodontic-6-Nitrile (II)

[0038] 6-chloroboxia (1.00 g, 7.2 mmol), anhydrous THF (5 mL) was added to 25 ml of three-necked flask, and stirred under nitrogen protection to dissolve, and the ice salt bath was at 0 ° C. Boron tedifer (1.13 g, 7.9 mmol) was added using a 5 ml syringe to maintain this temperature for 20 min. LiCl (0.42 g, 10.0 mmol) was added and stirring was continued for 5 min. Then, the liquid nitrogen is reduced to the temperature to reach -30 ° C. Under nitrogen protection was added to the syringe (8.6 mL, 1.0 M F, 8.6 mmol), and the internal temperature was -30 ° C. The temperature was stirred for 1 h. TLC monitoring shows that the raw material is completely transformed, and it is restored to room temperature. Dichloride (3.27 g, 14.4 mmol) was added, and stirring was continued for 2 h at the same temperature. After the TLC monitoring was complete, the reaction was added to the saturated ammonia (8 ml). Extraction was carried ou...

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Abstract

The invention discloses a synthesis method of 6-(4-methylpiperazine-1-yl)-4-o-tolyl nicotinamide, which comprises the following steps: (1) taking 6-chloronicotinonitrile as an initial raw material, carrying out nucleophilic addition reaction on the initial raw material and a reagent A in the presence of a boron trifluoride reagent, and after the reaction is completed, adding an oxidizing agent to carry out oxidation reaction to obtain a compound (II); the reagent A is o-tolyl magnesium halide or a combination of o-tolyl magnesium halide and lithium chloride; (2) condensing the compound (II) and N-methyl piperazine to generate a compound (III); (3) carrying out hydrolysis reaction on the compound (III) and hydrogen peroxide under the action of alkali to generate a compound (IV); the method is simple in reaction route, mild in reaction condition, high in product yield and suitable for industrial production.

Description

First, technical fields: [0001] The present invention relates to the synthesis of the pharmaceutical intermediate, and more particularly to the synthesis of 6- (4-methylpiperazine-1-yl) -4-xylene otteramide. Second, background technology: [0002] Structure, Netupitant, which is shown in the formula (V), is a highly selective P material / neurobide-1 (NK-1) receptor antagonist, has good tolerance, is prevention An important choice for nausea and vomiting symptoms caused by acute and delayed chemotherapy. It is used in combination with Palono Siqion, as a compound capsule for nausea and vomiting related to cancer chemotherapy. The drug trade name is Akynzeo, which is developed by Helsinn (Chinese name Helson). The drug was approved by the US Food and Drug Administration (ie FDA) on October 10, 2014. [0003] [0004] The 6- (4-methylpiperazine-1-yl) -4-4-o-chlorophenyl oxamide described herein is an important synthetic fragment in its molecular structure. [0005] The synthesis ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/82
CPCC07D213/82
Inventor 李景华方靓琦李彦辉
Owner ZHEJIANG UNIV OF TECH
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