Synthesis method of (R)-3-chloropyridyl-2-trifluoroethylamine hydrochloride

A technology of trifluoroethylamine hydrochloride and chloropyridyl, which is applied in the field of synthesis of -3-chloropyridyl-2-trifluoroethylamine hydrochloride, can solve problems such as limited quantity, achieve less waste and improve Effect of conversion rate and safety, availability of raw materials

Inactive Publication Date: 2021-04-20
BIRDO (SHANGHAI) PHARMATECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] It can be seen from the market research results that the number of domestic and foreign suppliers of (R)-3-chloropyridyl-2-trifluoroethylamine hydrochloride is very limited, and there is no documented

Method used

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  • Synthesis method of (R)-3-chloropyridyl-2-trifluoroethylamine hydrochloride
  • Synthesis method of (R)-3-chloropyridyl-2-trifluoroethylamine hydrochloride
  • Synthesis method of (R)-3-chloropyridyl-2-trifluoroethylamine hydrochloride

Examples

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Embodiment 1

[0069] In this example, the racemate 3-chloropyridyl-2-trifluoroethylamine hydrochloride was prepared through the following steps, and the reaction scheme is as follows:

[0070]

[0071] (1) Transport raw material SM through plunger pump 1 with a flow rate of 6mL / min as Feed 1; TMPMgCl.LiCl is dissolved in THF solution with a concentration of 1mol / L and transported through plunger pump 2 with a flow rate of 69.6mL / min , as Feed 2; build fixtures such as figure 1 As shown, set the molar ratio of Feed 1 and 2 to 1:1.1, set the temperature to 0-20°C, turn on the injection pump, the reaction starts, and the residence time is 30s to 1min; the DMF is transported through the plunger pump 3 with a flow rate of 7.3 mL / min, as Feed 3; mix with Feed 3 at the outlet of the microchannel; increase mechanical stirring in the reaction bottle; after the reaction, pour into ice water to quench, add 2N dilute hydrochloric acid to adjust the pH value to 8; add diatomaceous earth , stirred ev...

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Abstract

The invention discloses a synthesis method of (R)-3-chloropyridyl-2-trifluoroethylamine hydrochloride, and the synthesis method is characterized in that a Grignard reaction, a chiral induction addition reaction and a deprotection reaction are sequentially carried out to finally prepare a finished product. The invention provides a brand-new synthesis method of the (R)-3-chloropyridyl-2-trifluoroethylamine hydrochloride for the first time. The synthetic method is short in route, raw materials are easy to obtain, operation is easy, a continuous flow microreactor technology is adopted in the first step, reactants are rapidly and effectively mixed, the reaction time and the reaction temperature are accurately controlled, side reactions are avoided, and the conversion rate and safety are effectively improved. The compound 4 with high chiral purity is obtained through chiral induction addition reaction and recrystallization purification, and the de value of the compound 4 is greater than 99.5%. The post-treatment method is simple in post-treatment operation, column chromatography treatment is not needed after each step of reaction, reactants can be purified only through washing and extraction of a solvent, and the method is a novel post-treatment purification method.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis technology, specifically relates to a method for synthesizing (R)-3-chloropyridyl-2-trifluoroethylamine hydrochloride, and belongs to the field of synthesizing pharmaceutical intermediates. Background technique [0002] (R)-3-Chloropyridyl-2-trifluoroethylamine hydrochloride is an important intermediate, which plays an irreplaceable role in the synthesis of pharmaceuticals and pesticides. Molecular formula is C 7 h 7 Cl 2 f 3 N 2 , the molecular weight is 247.04, and the CAS number is 2089671-65-6. Calcium channels are transmembrane, multisubunit proteins that control Ca 2+ Enter the cell from the extracellular fluid. Almost all excitable cells in the human body, such as neurons of the central nervous system, peripheral nerve cells, and muscle cells, including cells of skeletal muscle, cardiac muscle, and smooth muscle of veins and arteries, have voltage-dependent calcium channels...

Claims

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Application Information

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IPC IPC(8): C07D213/61
Inventor 王雷许智郑子圣张宇超张奇
Owner BIRDO (SHANGHAI) PHARMATECH CO LTD
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