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Thiadiazine compound and asymmetric synthetic method thereof

A synthesis method, thiadiazine technology, applied in the field of catalytic asymmetric synthesis of thiadiazine compounds, can solve the problems of long reaction time, high cost, cumbersome synthesis, etc., and achieve the effect of short reaction time and mild reaction conditions

Active Publication Date: 2016-02-03
CHINA THREE GORGES UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method uses chiral phosphoric acid (BINOL-PA) with a large steric hindrance in the ortho position as a catalyst (complex synthesis and high cost), and the reaction time is as long as one week, so it has no application value

Method used

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  • Thiadiazine compound and asymmetric synthetic method thereof
  • Thiadiazine compound and asymmetric synthetic method thereof
  • Thiadiazine compound and asymmetric synthetic method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Add Sc(OTf) to the Schlenk tube 3 (7.4mg, 0.015mmol), chiral ligand L1 (6.8mg, 0.0225mmol) and freshly distilled dichloromethane 1.0mL, react at room temperature for 1 hour, add anthranilamide (26mg, 0.15mmol), isopentyl Aldehyde (20mg, 0.225mmol) and 30mg Molecular sieves were reacted at -40°C for 24 hours and separated by silica gel column chromatography to obtain 13.7 mg of a white solid with a yield of 38% and an ee value of 66%. 1 HNMR (400MHz, DMSO) δ = 7.46 (dd, J 1 =8.0Hz,J 2 =1.2Hz,1H),7.40(d,J=11.2Hz,1H),7.31-7.27(m,1H),6.97(s,1H),6.82(d,J=8.0Hz,1H),6.71(dt ,J 1 =8.0Hz,J 2 =0.4Hz,1H),4.71(s,1H),1.92-1.85(m,1H),1.73-1.66(m,1H),1.62-1.55(m,1H),0.96-0.93(m,6H); 13 CNMR (100MHz, DMSO) δ=144.25, 133.16, 124.20, 121.77, 116.74, 116.45, 64.55, 42.54, 23.91, 23.18, 22.34.

Embodiment 2

[0024] Add Sc(OTf) to the Schlenk tube 3 (7.4mg, 0.015mmol), chiral ligand L3 (8.3mg, 0.0225mmol) and freshly distilled dichloromethane 1.0mL, react at room temperature for 1 hour, add anthranilamide (26mg, 0.15mmol), isopentyl Aldehyde (20mg, 0.225mmol) and 30mg Molecular sieves were reacted at -40°C for 24 hours and separated by silica gel column chromatography to obtain 18.0 mg of a white solid with a yield of 50% and an ee value of 83%.

Embodiment 3

[0026] Add Sc(OTf) to the Schlenk tube 3 (7.4mg, 0.015mmol), chiral ligand L5 (8.9mg, 0.0225mmol) and freshly distilled dichloromethane 1.0mL, react at room temperature for 1 hour, add anthranilamide (26mg, 0.15mmol), isopentyl Aldehyde (20mg, 0.225mmol) and 30mg Molecular sieves were reacted at -40°C for 24 hours and separated by silica gel column chromatography to obtain 21.2 mg of a white solid with a yield of 59% and an ee value of 85%.

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Abstract

The invention relates to a thiadiazine compound and an asymmetric synthetic method thereof. According to the method, transition metal and chiral oxazoline ligand complexes are used as catalysts, orthanilamide and aldehyde are used as reactants, and condensation and asymmetric addition are performed, so as to obtain the chiral thiadiazine compound. The method has important application prospect in synthesizing chiral thiadiazine diuretic drugs.

Description

technical field [0001] The invention belongs to the field of organic synthesis methods, and in particular relates to a catalytic asymmetric synthesis method of thiadiazine compounds. Background technique [0002] Thiadiazines are commonly used intermediate-effect diuretics, and their main effects are diuretic and antihypertensive. Guidotti's research group obtained a single enantiomer of thiadiazine compounds by chiral resolution, and conducted animal experiments. The results showed that the activity of the right-handed enantiomer is higher than that of the left-handed enantiomer. (J. Pharm. Sci. 1995, 84, 937). At present, nearly 20 kinds of thiadiazine diuretics on the market, such as cyclopentadiazine, thiadiazine, and flubenzadiazine, are all racemates (Newly edited Pharmacology; edited by Chen Xinqian et al.). High curative effect, less toxic and side effects, and less dosage are the current trend of drug research. Chiral drugs meet these requirements and are the dire...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D285/28C07D285/24
CPCC07D285/24C07D285/28
Inventor 周海峰杜鹏隋月波蔡蓉邹坤
Owner CHINA THREE GORGES UNIV
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