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Making method of t-butyloxycarboryl-3-(hydroxymethyl)-[1,2,3]triazole[1,5-a]piperidine-6-amide

A technology of tert-butoxycarbonyl and hydroxymethyl, applied in tert-butoxycarbonyl‑3‑(hydroxymethyl)‑[1,2,3]triazole[1,5‑a]piperidine‑6‑ In the field of amide production method, it can solve the problems of no suitable industrial synthesis method, and achieve the effect of reasonable reaction process design, easy reaction and short route

Active Publication Date: 2017-09-26
武汉药明康德新药开发有限公司
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Problems solved by technology

Mainly solve the technical problem that there is no suitable industrial synthesis method at present

Method used

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  • Making method of t-butyloxycarboryl-3-(hydroxymethyl)-[1,2,3]triazole[1,5-a]piperidine-6-amide
  • Making method of t-butyloxycarboryl-3-(hydroxymethyl)-[1,2,3]triazole[1,5-a]piperidine-6-amide

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Embodiment 1

[0012] Sodium hydride (50.46 g, 1.26 mol ) was dissolved in tetrahydrofuran (1.5 L) in batches, then tert-butyl ethyl malonate (142.47 g, 756.91 mmol) was added dropwise at room temperature, stirred for one hour, and then added in batches Compound 1 was then reacted at 70° C. for 16 hours, and TLC (petroleum ether / ethyl acetate volume ratio=10 / 1) showed that the reaction was complete. The reaction system was cooled to 0°C, quenched by adding 1L of water, and then extracted with ethyl acetate (3*1L), the organic phase was washed with brine, then dried and concentrated to obtain crude compound 2 (247.5 g).

[0013] Mixture 2 (990.00 g, 3.19 mol) was dissolved in dichloromethane (5.0 L), and trifluoroacetic acid (600 mL) was added dropwise at 0°C. React at 25°C for 16 hours. TLC (petroleum ether / ethyl acetate volume ratio=5 / 1) showed that the reaction was complete. Then the pH of the reaction system was adjusted to 9-10 with saturated sodium carbonate aqueous solution. Then th...

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Abstract

The invention relates to a synthesis method of t-butyloxycarboryl-3-(hydroxymethyl)-[1,2,3]triazole[1,5-a]piperidine-6-amide. The technical problem that a suitable industrial synthesis method does not exist at present is mainly solved. The synthesis method is divided into the following seven steps of firstly making (2-chloro-5-nitropyridine) and t-butyl ethyl malonate react in a solvent tetrahydrofuran under the action of NaH to obtain a compound 2; obtaining a compound 3 from the compound 2 under the action of trifluoroacetic acid; afterwards, subjecting the compound 3 to a hydrogenation reaction under the catalysis of palladium carbon to obtain a compound 4; carrying out t-butyloxycarboryl protection on the compound 4 to obtain a compound 5; making the compound 5 act with p-ABSA (p-Acetamidobenzenesulfonyl Azide) under the action of DBU (1,8-Diazabicyclo[5,4,0]undec-7-ene) to obtain a compound 6; reducing the compound 6 in the tetrahydrofuran by lithium aluminium tetrahydride to obtain a compound 7; subjecting the compound 7 to catalytic hydrogenation under the catalysis of wet palladium carbon to obtain a final compound 8.

Description

technical field [0001] The invention relates to a synthesis method of compound tert-butoxycarbonyl-3-(hydroxymethyl)-[1,2,3]triazol[1,5-a]piperidine-6-amide. Background technique [0002] The compound tert-butoxycarbonyl-3-(hydroxymethyl)-[1,2,3]triazol[1,5-a]piperidine-6-amide (MFCD28390423) and related derivatives in medicinal chemistry and organic Widely used in synthesis. At present, there are few reports on the synthesis methods of tert-butoxycarbonyl-3-(hydroxymethyl)-[1,2,3]triazol[1,5-a]piperidine-6-amide. Therefore, it is necessary to develop a synthetic method that is easy to obtain raw materials, easy to operate, easy to control the reaction, suitable for overall yield, and suitable for industrial production. Contents of the invention [0003] The purpose of this invention is to develop a kind of raw material that is easy to get, easy to operate, and the reaction is easy to control, and the higher tert-butoxycarbonyl-3-(hydroxymethyl)-[1,2,3]triazole[1 , 5-a]...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 韩冰洋杨云龙高文帅王海林杜记杨承驹于凌波马汝建
Owner 武汉药明康德新药开发有限公司
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