Supercharge Your Innovation With Domain-Expert AI Agents!

N-acetyl-(N-difluoroethyl) amide compound and preparation method thereof

A technology of amide compounds and difluoroethyl, which is applied in the field of preparation of N-acetyl-amide compounds, can solve the problems of less by-products in product yield, cumbersome preparation process, harsh reaction conditions, etc., and achieve less side reactions, The process is easy to operate and the effect of easy operation

Inactive Publication Date: 2018-06-08
JIANGXI NORMAL UNIV
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Aiming at defects such as cumbersome raw material preparation process, harsh reaction conditions and scarcity of methods used in the synthesis process of existing N-acetyl-(N-difluoroethyl) amides, the object of the present invention is to provide a method that does not require the use of A method for preparing N-acetyl-(N-difluoroethyl)amide compounds with metal catalysis or cheap metal catalysis, mild reaction conditions, high product yield, and few by-products. This method is designed and synthesized with a new structure N-acetyl-(N-difluoroethyl)amide compounds provide raw material sources for materials, drug screening and new drug synthesis

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • N-acetyl-(N-difluoroethyl) amide compound and preparation method thereof
  • N-acetyl-(N-difluoroethyl) amide compound and preparation method thereof
  • N-acetyl-(N-difluoroethyl) amide compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～14

[0031] The following implementations 1-14 are prepared according to the following synthetic route, and compounds 1-14 can be prepared:

[0032]

Embodiment 1

[0034] Benzoic acid (24.5mg, 0.2mmol, 1equiv) and Cu(OTf) 2 (3.6mg, 0.01mmol, 5mol%) was dissolved in MeCN (5ml); at room temperature, tert-butyl nitrite (62μL, 0.5mmol, 2.5equiv) and 2,2-difluoroethylamine (38μL, 0.5mmol , 2.5 equiv) stirring, the temperature was raised to 65° C. and the reaction was continued for 12 hours. After the reaction was complete, spin-dried under reduced pressure, and separated by silica gel flash column chromatography to obtain the target compound 1 (40 mg, 0.173 mmol).

[0035] Substrate: Benzoic acid

[0036] product:

[0037] Compound 1: colorless oil (40mg, 87% yield); IR(KBr)ν max / cm -1 :3064,2977,1696,1671, 1598,1451,1339,1221,1117,1019,855,703; 1 H NMR (400MHz, CDCl 3 )δ7.64 (tt, J=5.7, 1.3 Hz, 2H), 7.62–7.58 (m, 1H), 7.53–7.47 (m, 2H), 6.08 (tt, J=56.8, 4.5Hz, 1H), 4.15 (td, J=13.5, 4.5Hz, 2H), 2.15(s, 3H); 13 C NMR (100MHz, CDCl 3 )δ173.7, 173.3, 134.7, 133.1, 129.1, 128.7, 113.2 (t, J = 242.8Hz), 47.8 (t, J = 28.6Hz), 25.9; 1...

Embodiment 2

[0039] p-Fluorobenzoic acid (28mg, 0.2mmol, 1equiv) and Cu(OTf) 2 (3.6mg, 0.01mmol, 5mol%) was dissolved in MeCN (5ml), and at room temperature, tert-butyl nitrite (62μL, 0.5mmol, 2.5equiv) and 2,2-difluoroethylamine (38μL, 0.5mmol, 2.5 equiv) stirring, the temperature was raised to 80° C. and the reaction was continued for 20 hours. After the reaction was complete, spin-dried under reduced pressure, and separated by silica gel flash column chromatography to obtain the target compound 2 (42 mg, 0.164 mmol).

[0040] Substrate: p-Fluorobenzoic acid

[0041] product:

[0042] Compound 2: pale yellow oil (42mg, 82% yield); IR(KBr)ν max / cm -1 :3369,2922,2850,1707, 1676,1602,1507,1410,1337,1234,1219,1116,1026,986,852,770; 1 H NMR (400MHz, CDCl 3 ) δ7.81–7.61(m,2H),7.26–7.08(m,2H),6.07(tt,J=56.7,4.4Hz,1H),4.13(td,J=13.6,4.4Hz,2H),2.16 (s,3H); 13 C NMR (100MHz, CDCl 3 )δ 173.0, 172.6, 166.8, 164.2, 131.3 (d, J = 9.2 Hz), 130.8 (d, J = 3.3 Hz), 116.4 (d, J = 22.2 Hz), 113....

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses an N-acetyl-(N-difluoroethyl) amide compound and a preparation method thereof by a one-pot method. The preparation method comprises the step of reacting carboxylic acid, tert-butyl nitrite and 2,2-difluoroethylamine through the one-pot method under the condition that a catalytic amount of copper trifluoromethanesulfonate is added in acetonitrile to obtain the N-acetyl-(N-difluoroethyl) amide compound. The preparation method is simple to operate, mild in reaction condition, low in cost, less in byproduct and high in yield, can obtain an aromatic and aliphatic N-acetyl-(N-difluoroethyl) amide compound and is not limited by a substrate, so that an N-acetyl groups-(N-difluoroethyl) amide compound library is established, and a raw material source is provided for drug screening and new drug synthesis.

Description

technical field [0001] The invention relates to a method for preparing N-acetyl-(N-difluoroethyl) amides in one step and one pot, in particular to the preparation of N-acetyl by using carboxylic acid and 2,2-difluoroethylamine as raw materials A method for (N-difluoroethyl) amide compounds, belonging to the technical fields of fluorine chemistry, material chemistry and pharmaceutical intermediate synthesis. Background technique [0002] In recent years, 20% of drugs and 30% of pesticides on the market contain at least one fluorine atom. Many fluorine-containing compounds have special properties due to the introduction of fluorine atoms, and have attracted more and more attention from scientists. N-difluoroethylimides, as a class of compounds introducing fluorine atoms, have high reaction rate, excellent selectivity, product specificity, and the characteristics of cheap and easy-to-obtain catalysts. Chemistry, heterocyclic chemistry, medicinal chemistry, materials chemistry...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07C233/91C07C233/92C07C231/02C07D333/38C07D307/68
CPCC07C233/91C07C233/92C07D307/68C07D333/38
Inventor 胡祥国彭山青高玉刘德永
Owner JIANGXI NORMAL UNIV
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com