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A kind of deuterated dimethylhydroxylamine benzoate compound and its preparation method and application

A technology for dimethylhydroxylamine benzoic acid and ester compounds, which is applied in the field of novel deuterated dimethylhydroxylamine benzoic acid ester compounds and their preparation, and achieves the effects of fast reaction rate, high yield and mild conditions

Active Publication Date: 2020-11-10
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] At present, there is no good method for synthesizing deuterated dimethylamine compounds

Method used

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  • A kind of deuterated dimethylhydroxylamine benzoate compound and its preparation method and application
  • A kind of deuterated dimethylhydroxylamine benzoate compound and its preparation method and application
  • A kind of deuterated dimethylhydroxylamine benzoate compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] O-benzoyl-N,N-di(methyl-d 3 ) Preparation of hydroxylamine:

[0037] 100mL Schlenk tube, replaced with argon three times. Add 600mg (15mmol) of sodium hydride (NaH) and 10mL of anhydrous N,N-dimethylformamide under the protection of argon, and cool to 0°C. Then 600 mg (5 mmol) of tert-butyl carbamate was dissolved in 10 mL of anhydrous N,N-dimethylformamide, and slowly injected into the Schlenk tube. Finally, 2.2 g (15 mmol) of deuteroiodomethane was dissolved in 10 mL of anhydrous N,N-dimethylformamide, slowly injected into the Schlenk tube, and reacted at 0° C. for 3 hours. After the reaction was completed, the reaction solution was quenched with water (150 mL), followed by extraction with 50 mL of diethyl ether three times. The organic phase was collected and washed twice with 50 mL of water. Concentration of the organic phase afforded tert-butylbis(methyl-d 3 ) carbamate.

[0038] The resulting tert-butylbis(methyl-d 3 ) carbamate, cooled to 0°C, and 10 mL of...

Embodiment 2

[0042] O-(4-fluorobenzoyl)-N,N-di(methyl-d 3 ) Preparation of hydroxylamine:

[0043] 100mL Schlenk tube, replaced with argon three times. Add 600mg (15mmol) of sodium hydride (NaH) and 10mL of anhydrous N,N-dimethylformamide under the protection of argon, and cool to 0°C. Then 600 mg (5 mmol) of tert-butyl carbamate was dissolved in 10 mL of anhydrous N,N-dimethylformamide, and slowly injected into the Schlenk tube. Finally, 2.2 g (15 mmol) of deuteroiodomethane was dissolved in 10 mL of anhydrous N,N-dimethylformamide, slowly injected into the Schlenk tube, and reacted at 0° C. for 3 hours. After the reaction was completed, the reaction solution was quenched with water (150 mL), followed by extraction with 50 mL of diethyl ether three times. The organic phase was collected and washed twice with 50 mL of water. Concentration of the organic phase afforded tert-butylbis(methyl-d 3 ) carbamate.

[0044] The resulting tert-butylbis(methyl-d 3 ) carbamate, cooled to 0°C, an...

Embodiment 3

[0048] O-(3,4-dichlorobenzoyl)-N,N-di(methyl-d 3 ) Preparation of hydroxylamine:

[0049] 100mL Schlenk tube, replaced with argon three times. Add 600mg (15mmol) of sodium hydride (NaH) and 10mL of anhydrous N,N-dimethylformamide under the protection of argon, and cool to 0°C. Then 600 mg (5 mmol) of tert-butyl carbamate was dissolved in 10 mL of anhydrous N,N-dimethylformamide, and slowly injected into the Schlenk tube. Finally, 2.2 g (15 mmol) of deuteroiodomethane was dissolved in 10 mL of anhydrous N,N-dimethylformamide, slowly injected into the Schlenk tube, and reacted at 0° C. for 3 hours. After the reaction was completed, the reaction solution was quenched with water (150 mL), followed by extraction with 50 mL of diethyl ether three times. The organic phase was collected and washed twice with 50 mL of water. Concentration of the organic phase afforded tert-butylbis(methyl-d 3 ) carbamate.

[0050] The resulting tert-butylbis(methyl-d 3 ) carbamate, cooled to 0°C...

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Abstract

The invention provides a deuterated dimethylhydroxylamine benzoate compound and a preparation method and application thereof. The compound has the following structural formula as shown in the description, wherein R1, R2, R3, R4 and R5 represent hydrogen or , methoxyl or , benzyloxy or, methyl or, phenyl or, fluorine or, chlorine or, bromine or, trifluoromethyl, or oxytrifluoromethyloxy or, nitrylor, cyano or sulfonyl separately and independently; the method comprises the preparation steps that in the presence of inorganic salt, deuterated dimethylamine salt and benzoyl peroxide or a derivative of the benzoyl peroxide are protected from light react in an organic solvent, at 15-35 DEG C without light, reaction is carried out for 15-20 h, and then quenching reaction is carried out; the inorganic salt is alkali metal salt. The compound can be used as a deuterated dimethylamine agent for participating in synthsis of deuterated dimethylamine aryl compounds. A The synthesis strategy has thecharacteristics that the conditions are mild, the yield is high, the reaction rate is high, a the deuterated ratio is high, and the like.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a novel deuterated dimethylhydroxylamine benzoate compound and its preparation method and application. Background technique [0002] Deuterium is a stable isotope of hydrogen. Deuterium can form stronger chemical bonds than hydrogen, making drug molecules more stable. Human trials have found that deuterium substitution can change the characteristics of the drug, such as half-life (reducing the number of doses, which can reduce the dose), absorption, distribution and toxicity, while maintaining the original activity and selectivity. Deuterium-substituted drugs have become a new direction for new drug research and development, and are a simple and effective drug development model. In 2017, the U.S. Food and Drug Administration approved the world's first deuterated drug deuterated tetrabenazine (AUSTEDO TM ) (Treatment of Huntington's disease and associated motor dys...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C291/04C07C209/22C07C209/00C07C211/52C07C269/06C07C271/22C07J1/00C07K7/06
CPCC07B2200/05C07C209/00C07C209/22C07C269/06C07C291/04C07J1/0096C07K7/06C07C211/52C07C271/22
Inventor 史壮志陈成赵斌林
Owner NANJING UNIV
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