Unlock instant, AI-driven research and patent intelligence for your innovation.

Preparation method of heterocyclic compound and salt thereof

A technology for heterocyclic compounds and compounds, applied in the field of organic chemical synthesis, can solve problems such as unfavorable industrial production, cumbersome preparation routes, etc.

Active Publication Date: 2019-06-04
BTC PHARMA TECH CO LTD +1
View PDF4 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In addition, the preparation route of the existing process is cumbersome, and the raw material compound needs to go through the steps of protecting group, alkylation, reduction and deprotection group to obtain the target product, which is not conducive to industrial production

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method of heterocyclic compound and salt thereof
  • Preparation method of heterocyclic compound and salt thereof
  • Preparation method of heterocyclic compound and salt thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0146]

[0147] Weigh 10g of tetrahydropyran-4-cyano-4-carboxylic acid 1 into 50mL of N,N-dimethylformamide (DMF) and stir to dissolve, then gradually add 15mL of triethylamine, continue stirring for about 5min, Gradually add 40g diphenylphosphoryl azide (DPPA) dropwise. After the dropwise addition, stir the reaction at room temperature. After about 3 hours of reaction, TLC monitors the reaction and shows that the reaction conversion is complete. The prepared acyl azide compound is directly used for subsequent feeding without separation. , and then add 200mL of tert-butanol to the system, then gradually raise the temperature of the system to 110°C for reaction, the system will generate gas during the reaction, stop the reaction after about 8 hours of reaction, put the system on a rotary evaporator to spin off the system solvent, The remaining brown oily liquid was dissolved in ethyl acetate, washed once with saturated sodium bicarbonate solution, and then the organic phase w...

Embodiment 2

[0149]

[0150] Weigh 5g of Compound 2 and dissolve it in 100mL of methanol, then place the system in an ice bath to cool, gradually add 50mL of 6M hydrochloric acid solution dropwise, continue to stir for 2 hours after the addition, after the reaction, put the system in a rotary evaporator The solvent in the system was spun off to obtain a dark white solid powder, which was purified on a silica gel column to obtain 1.7 g of a yellow oil, namely compound 3, with a yield of 61%.

Embodiment 3

[0152]

[0153] Put 11g of compound 2 in 200mL of DMF and stir to dissolve, then place the system in an ice bath to cool, then add 4g of 60% sodium hydride solid in batches, after the addition, continue to stir the system for 10min, then gradually add 10g of methyl iodide , after the addition, the system continued to stir for 10 min under ice bath, then placed at room temperature to stir the reaction, TLC monitored the reaction until the conversion of raw materials was complete, then added 20 mL of saturated sodium sulfite solution to quench the reaction, filtered the quenched system, and collected the filtrate , then the system solvent was removed, the residue was dissolved in ethyl acetate, the insoluble matter was filtered off, the filtrate was collected, and washed once with saturated sodium bicarbonate, the ethyl acetate phase was collected, and dried with anhydrous sodium sulfate, and the dried acetic acid The ethyl ester phase was collected and the solvent was spun of...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention belongs to the field of organic chemistry and specifically relates to a preparation method of a heterocyclic compound as shown in the formula I and salt thereof. In comparison with the prior art, the invention has the following beneficial effects: the use of the extremely toxic substance cyanide is avoided; there is no cyanide ion residue in the reaction product and the reaction waste such that environmental burden is greatly reduced. In addition, the price of the reaction materials is low; the preparation method is simple; the yield is high; and the preparation method is suitable for large-scale industrial production. It is found unexpectedly that by the adoption of the method of the scheme 4, such as use of a reducing agent and under the acidic condition, the compound VIIIcan be obtained by one-step reaction and the off-protecting group, alkylation and cyano group reduction are realized to obtain the target product. The defect that polystep reactions are required in the prior art is greatly improved.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis, and in particular relates to a preparation method of a heterocyclic compound and a salt thereof. Background technique [0002] The heterocyclic compound represented by the following formula I has important applications in pharmaceutical compounds and pesticide chemistry, and is an important class of advantageous building blocks. However, the current synthesis method usually uses the corresponding heterocyclic ketone as a raw material, condenses with a disubstituted amine, reacts with potassium cyanide to prepare the corresponding intermediate, and finally hydrogenates to obtain the target product. The specific process is shown in the following formula. At present, this method needs to use a large amount of highly toxic potassium cyanide, and the feeding process needs to be strictly protected. After the reaction, the content of cyanide ions in the waste liquid also needs to be detected an...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07D305/08C07D331/04C07D205/04C07D309/14C07D333/36C07D207/14C07D211/58
CPCY02P20/55
Inventor 蔡岩杨少强吴加朋李怀鑫周广徐本全
Owner BTC PHARMA TECH CO LTD