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Synthesis and purpose of amidine compound containing two chiral centers

A compound and chiral technology, applied in the field of synthesis of amidine compounds, can solve the problem of great harm of peppers and achieve good economic and social benefits

Active Publication Date: 2017-02-22
嘉兴慧泉生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, pepper bacterial wilt is extremely harmful to pepper

Method used

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  • Synthesis and purpose of amidine compound containing two chiral centers
  • Synthesis and purpose of amidine compound containing two chiral centers
  • Synthesis and purpose of amidine compound containing two chiral centers

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Example 1: Synthesis (6 R ,12a R )-2,3,6,7,12,12a-hexahydro-4-methylimino-2-methyl-6-(3,5-difluorophenyl)-pyrazin-1-one-[ 6,1:2',1']pyridine[3,4-b]indole (English name: (6 R ,12a R )-2,3,6,7,12,12a-Hexahydro-4-methylimino -2-methyl-6-(3,5-difulorophenyl)-piperazin-1-one-[6,1:2',1' ]pyrido[3,4-b]indole; MIPO-6-1 for short)

[0041] 1) Preparation of catalyst trimethylsilyl polyphosphate:

[0042] Under nitrogen protection, add 50ml of dried solvent dichloromethane, phosphorus pentoxide (14.2g, 50mmol), and hexamethyldisiloxane (25.6g, 160mmol) into a dry three-necked reaction flask, and heat to reflux. After reacting for 1 hour, the reflux reaction device was changed to a distillation reaction device, and the temperature was gradually raised to 160°C. During the heating process, the low boiling point solvent and unreacted hexamethyldisilyl ether were distilled out and kept at 160°C for 1 hour. The obtained syrupy liquid was 27.8 g (liquid is trimethylsilyl polyphosphate), i...

Embodiment 2

[0046] Example 2: Synthesis (6 R ,12a R )-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,5-difluorophenyl)-pyrazine-[6,1:2',1']pyridine [3,4-b]Indole-1,4-dione (English name: (6 R ,12a R )-2,3,6,7,12,12a-Hexahydro-2-methyl-6-(3,5-difuloro phenyl)-pyrazino-[6,1:2,1']pyrido[3,4-b ]indole-1,4-dione; referred to as B-6-1).

[0047]

[0048] The compound C-6-1((1R, 3R)methyl 2-(2-chloroacetyl)-1-(3,5-difluorophenyl) -2,3,4,9-tetrahy dro-1H- pyrido[3,4 -b]indole-3-carboxylate) (16.7g, 40mmol) was dissolved in 160 mL DMF. At room temperature, slowly add 30% methylamine aqueous solution (20.7g, 200mmol) to the solution, and the addition is complete Afterwards, it was stirred overnight at room temperature and monitored by thin layer chromatography. When the reaction of the raw material C-6 was complete, the reaction was stopped. Add 500 grams of ice-water mixture to another reaction flask, add the above reaction liquid dropwise to the ice-water mixture under vigorous stirring, let stand, filter...

Embodiment 3

[0049] Example 3: Synthesis of (1R, 3R)-2-(2-chloroacetyl)-1-(3,5-difluorophenyl)-2,3,4,9-tetrahydro-1H-pyridine [3 ,4-b)Indole-3-carboxylic acid methyl ester (English name: (1R, 3R)-methyl 2-(2-chloroacetyl)-1- (3,5-difluorophenyl)-2,3,4,9 -tetrahydro-1H-pyrido [3,4-b] indole -3-carboxylate; referred to as C-6-1).

[0050]

[0051] In a three-necked flask equipped with mechanical stirring, add E-6-1((1R, 3R)-methyl 1-(3,5-difluorophenyl)-2,3,4,9-tetrahydro- 1H-pyrido[3 ,4-b]indole-3-carboxylate) hydrochloride (37.9 g, 100 mmol), triethylamine (30.4 g, 300 mmol), 500 mL of dichloromethane, stir at room temperature for half an hour, the solution becomes clear and transparent. Using an ice-salt bath, the temperature of the reaction system was lowered to 0°C, chloroacetyl chloride (16.9 g, 150 mmol) was added dropwise, and the addition was kept at 0-5°C. After the addition is completed, the reaction is stirred at 0~5°C and monitored by thin layer chromatography. When the reaction ...

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Abstract

The invention discloses a synthesis method of 1-methyl-5--methylimino-piperazin-2-ketone derivative compound with the general formula being MIPO and containing two chiral centers, and application of the compound. The target compound with the general formula being MIPO is obtained from a compound of H2NR<2> (ammonia or substituted ammonia) with the general formula being A and a compound (1-piperazin-1,4-diketone derivative compound) with the general formula being B through reaction, wherein substitutes of R1, R2 and R3 in the general formulas A and B are identical to those in the general formula MIPO. The compound with the general formula being MIPO can be used as an effective ingredient of a sterilizing agent.

Description

Technical field [0001] The invention relates to the synthesis and use of amidine compounds, in particular to the synthesis and sterilization use of a class of amidine compounds containing two chiral centers. Background technique [0002] Amidine has a wide range of applications in medicine, and can be used as a drug for the treatment of diabetes, cardiovascular diseases, anti-inflammatory drugs, anthelmintics and diuretics. For example, the cyclic amidine compound described in Formula 1 has a vasodilator effect and is used to treat hypertension. The aryl-substituted amidine compound containing multiple iodine described in formula 2 has high selectivity to tuberculosis fungi, and its cholangiodime sodium is an oral gall bladder and cholangiocontrast drug. It has low toxicity, few side effects and is safe for patients. Compared with traditional medicine, the imaging is fast, the patient does not need to eat, and the imaging effect is good. In addition, some amidine compounds hav...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/14A01N43/90A01P3/00
CPCA01N43/90C07B2200/07C07D471/14
Inventor 杨维清李洪洋王会镇
Owner 嘉兴慧泉生物科技有限公司
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