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Preparation method of 3-(2-phenethyl)-2-pyridinecarboxamide compound

A picolinamide and compound technology, which is applied in the field of preparation of 3--2-pyridinecarboxamide compounds, can solve the problems of low yield, preparation limitation, and difficulty in obtaining reaction raw materials.

Inactive Publication Date: 2018-01-09
SICHUAN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] The raw materials used in this method are not easy to get, resulting in high preparation cost
[0013] In summary, the existing methods for preparing 3-(2-phenylethyl)-2-pyridinecarboxamides (I) have the disadvantages that the reaction raw materials are not easy to obtain, the reaction conditions are harsh, the reaction operation and post-treatment process are cumbersome, and the environment Problems such as serious pollution and low yield limit its mass production

Method used

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  • Preparation method of 3-(2-phenethyl)-2-pyridinecarboxamide compound
  • Preparation method of 3-(2-phenethyl)-2-pyridinecarboxamide compound
  • Preparation method of 3-(2-phenethyl)-2-pyridinecarboxamide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Preparation of 3-[2-(3-chlorophenyl)vinyl]-2-pyridinecarboxamide (3-17)

[0040] Add 2-cyano-3-picoline (10.0 mmol), 3-chlorobenzaldehyde (12.0 mmol) and N,N - Dimethylformamide (25 ml), after stirring evenly, add lithium hydroxide (3.0 mmol), stir the reaction at room temperature (the reaction progress is monitored by TLC), and the reaction is complete in about 24 h. After the reaction was completed, deionized water (50.0 ml) was added and extracted several times with ethyl acetate; the organic layers were combined and washed with deionized water and saturated NaCl aqueous solution; the organic layer was washed with anhydrous NaCl 2 SO 4 Dry, filter, evaporate the solvent under reduced pressure, and recrystallize the residue to obtain an off-white solid with a yield of 48.0%; mp 149~150 °C; 1 H NMR (CDCl 3 )d:8.48(d, J =4.4 Hz, 1H), 8.43(d, J =16.4 Hz, 1H), 8.04(d, J =8.0 Hz, 1H), 7.97(brs, 1H), 7.55(s, 1H), 7.46(dd, J =4.4 Hz, 8.0 Hz, 1H), 7.45(d, J =8.0 Hz,1...

Embodiment 2

[0042] Preparation of 3-[2-(3-chlorophenyl)vinyl]-2-pyridinecarboxamide (3-17)

[0043] The operation process was the same as in Example 1, except that lithium hydroxide was replaced by sodium hydroxide to obtain an off-white solid with a yield of 46.5%; its chemical structure was confirmed by NMR.

Embodiment 3

[0045] Preparation of 3-[2-(3-chlorophenyl)vinyl]-2-pyridinecarboxamide (3-17)

[0046] The operation process was the same as in Example 1, except that lithium hydroxide was replaced by potassium hydroxide to obtain an off-white solid with a yield of 54.0%; its chemical structure was confirmed by NMR.

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Abstract

The invention discloses a preparation method of a 3-(2-phenethyl)-2-pyridinecarboxamide compound (I). The preparation method comprises the following steps: taking 2-cyano-3-methylpyridine and a benzaldehyde compound as starting raw materials, firstly performing a condensation reaction in an appropriate solvent and under an alkali condition to obtain a 3-(2-styryl)-2-pyridinecarboxamide compound, then performing a catalytic hydrogenation reaction on the intermediate to obtain the 3-(2-phenethyl)-2-pyridinecarboxamide compound (I).

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and relates to a preparation method of a class of 3-(2-phenylethyl)-2-pyridinecarboxamide compounds whose chemical structure is shown in (I). [0002] [0003] Where: R 1 and R 2 Each independently represents H, OH, C 1-12 Alkyl, C 1-12 Alkoxy, CH 3 OCH 2 O, F, Cl, Br, CF 3 、OCF 3 、CONH 2 , NH 2 、N(Me) 2 , NHCOR 5 , R 5 means H, C 1-12 Alkyl; R 1 and R 2 Any possible position on the benzene ring. Background technique [0004] 3-(2-phenylethyl)-2-pyridine carboxamide compound (I) is a synthetic tricyclic H 1 Important intermediates of receptor antagonists (Villani F.J. et al. J. Med. Chem. , 1972, 15(7), 750-754; Villani F.J. et al. US 4659716), the preparation method of such compounds disclosed in the current literature is mainly based on 2-cyano-3-picoline (1) or 3-(2-phenylethyl)-2-pyridinecarbonitrile compounds Starting raw material, its specific synthetic method is ...

Claims

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Application Information

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IPC IPC(8): C07D213/81
Inventor 邓勇徐锐宋青刘红艳
Owner SICHUAN UNIV
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