A kind of synthetic method of 5-amino-3-cyanopyridine carboxylic acid methyl ester hydrochloride

A technology of cyanopicolinic acid and methyl ester hydrochloride is applied in the field of synthesis of 5-amino-3-cyanopicolinate methyl ester hydrochloride, and achieves the effects of high yield, simple operation and short route.

Active Publication Date: 2022-03-08
阿里生物新材料(常州)有限公司
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Problems solved by technology

The synthetic method of 5-amino-3-cyanopicolinate methyl ester hydrochloride synthetic method rarely has bibliographical information at present

Method used

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  • A kind of synthetic method of 5-amino-3-cyanopyridine carboxylic acid methyl ester hydrochloride
  • A kind of synthetic method of 5-amino-3-cyanopyridine carboxylic acid methyl ester hydrochloride

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preparation example Construction

[0019] A kind of synthetic method of 5-amino-3-cyanopicolinate methyl ester hydrochloride, the method comprises the steps:

[0020] (1) According to compound A, tert-butyl carbamate, Pd 2 (dba) 3 , Xantphos, the mass ratio of potassium carbonate are 10:4~6:1~3:1~2:8~10, and the solid-liquid g / mL ratio of compound A and dioxane is 1:16, and the material is taken, Add compound A, tert-butyl carbamate, Pd to the reaction flask 2 (dba) 3 , Xantphos, potassium carbonate and dioxane, replaced by nitrogen 3 times, protected by nitrogen, heated to 85°C, and reacted for 12 hours to obtain compound B;

[0021] (2) According to compound B, triethylamine, Pd(dppf)Cl 2 The mass ratio of compound B and methanol is 5:5~7:0.3~1, the solid-liquid g / mL ratio of compound B and methanol is 1:20, and the material is taken, and compound B, triethylamine, Pd(dppf)Cl 2 Add methanol and methanol into the autoclave, feed CO into the reaction system, adjust the pressure to 0.7-0.9MPa, heat to 85-95...

Embodiment 1

[0024] A kind of synthetic method of 5-amino-3-cyanopicolinate methyl ester hydrochloride, the method comprises the steps:

[0025] (1) Add 10g of compound A, 6g of tert-butyl carbamate, 2g of Pd into the reaction flask 2 (dba) 3 , 1.5g Xantphos, 9g potassium carbonate and 160mL dioxane, nitrogen replacement 3 times, nitrogen protection, heated to 85°C, reacted for 12h, TLC detection, the reaction of the raw materials was completed, the reaction system was cooled to room temperature, filtered with a small amount of diatomaceous earth, Rinse the filter cake (80 mL) with ethyl acetate, spin the filtrate to dry, add ethyl acetate (200 mL), wash with saturated brine (80 mL), concentrate, mix the sample and pass through the column to obtain 10.8 g of yellow solid, compound B, yield 92.6% , with a purity of 96.2%;

[0026] (2) Mix 5g compound B, 6g triethylamine, 0.5g Pd(dppf)Cl 2 Add 100mL of methanol into the autoclave, feed CO into the reaction system, adjust the pressure to 0...

Embodiment 2

[0030] A kind of synthetic method of 5-amino-3-cyanopicolinate methyl ester hydrochloride, the method comprises the steps:

[0031] (1) Add 10g compound A, 5g tert-butyl carbamate, 1gPd to the reaction flask 2 (dba) 3 , 2gXantphos, 10g potassium carbonate and 160mL dioxane, nitrogen replacement 3 times, nitrogen protection, heated to 85°C, reacted for 12h, TLC detection, the reaction of the raw materials was completed, the reaction system was cooled to room temperature, filtered with a small amount of diatomaceous earth, acetic acid The filter cake (80 mL) was rinsed with ethyl ester, the filtrate was spin-dried, ethyl acetate (200 mL) was added, washed with saturated brine (80 mL), concentrated, mixed and passed through the column to obtain 10.3 g of a yellow solid. Compound B was obtained with a yield of 88.3% and a purity of 96.8%;

[0032] (2) Combine 5g of compound B, 7g of triethylamine, 1g of Pd(dppf)Cl 2 Add 100mL of methanol into the autoclave, feed CO into the rea...

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Abstract

The invention belongs to pharmaceutical intermediates, in particular to a method for synthesizing methyl 5-amino-3-cyanopyridine carboxylate hydrochloride. The present invention provides a kind of compound A as basic raw material, synthesized 5-amino-3-cyanopyridine carboxylate hydrochloride through three-step reaction, is 5-amino-3-cyanopyridine carboxylate hydrochloride The synthetic method of salt provides synthetic route; The synthetic method of 5-amino-3-cyanopicolinate methyl ester hydrochloride of the present invention is that route is brief, reasonable in design, and simple to operate, easy to control; The obtained product of the present invention obtains The rate is higher.

Description

technical field [0001] The invention belongs to pharmaceutical intermediates, in particular to a method for synthesizing methyl 5-amino-3-cyanopicolinate hydrochloride. Background technique [0002] The synthesis method of the compound 5-amino-3-cyanopyridine carboxylate hydrochloride and related derivatives are widely used in medicinal chemistry and organic synthesis. The synthetic method of methyl 5-amino-3-cyanopicolinate hydrochloride is rarely reported in the literature. 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] Technical problem to be solved by the present invention: Aiming at the problems described above, a synthetic method of methyl 5-amino-3-cyanopicolinate hydrochloride is provided. [0004] In order to solve the problems of the technologies described above, the...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/85
CPCC07D213/85
Inventor 许义波刘超
Owner 阿里生物新材料(常州)有限公司
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