Adamantyl pyridine carboxamide complexes, intermediates, preparation methods and applications thereof
A technology of adamantyl picolinamide and complexes, which can be used in copper organic compounds, drug combinations, antitoxic agents, etc., can solve the problems of high cost, easy to be hydrolyzed by protease, difficult to penetrate cell membrane and alloantigenicity, etc.
- Summary
- Abstract
- Description
- Claims
- Application Information
AI Technical Summary
Problems solved by technology
Method used
Image
Examples
preparation example Construction
[0054] In the preparation method of the above intermediate, in order to increase the yield of the contact reaction, preferably the contact reaction is carried out below 0°C, and the reaction temperature of the contact reaction is -10-0°C, preferably -3-0°C;
[0055] According to the present invention, in order to make the contact reaction fully proceed, the reaction time of the contact reaction is 3-20 h, preferably 10-15 h.
[0056] [ M(N3) 2 ]·6H 2 O carries out complex reaction;
[0057]
[0058] In formula (L1), n is 1-3, preferably, n is 1;
[0059] In the above formula, M is a divalent metal cation, and N3 is selected from perchlorate ion, hexafluorophosphate ion or tetrafluoroborate ion;
[0060] Preferably, M is Cu 2+ or Zn 2+ , N3 is perchlorate ion;
[0061] More preferably, the [M(N3) 2 ]·6H 2 O is Cu(ClO 4 ) 2 ·6H 2 O.
[0062] According to the present invention, the organic solvent only needs to be an organic solvent capable of dissolving the rea...
preparation example 1
[0072] Preparation of 1-adamantanyl chloride:
[0073] In a 250mL round-bottomed flask, add 10.0mmol of 1-adamantanecarboxylic acid solid and 60mL of anhydrous toluene solvent in sequence, and slowly add 20mL of thionyl chloride dropwise after magnetic stirring to dissolve, reflux at 80°C for 8 hours, and cool to 20°C , the solvent was removed by rotary evaporation, and 10 mL of anhydrous toluene was added three times, and the solvent and excess thionyl chloride were removed by rotary evaporation to obtain a light yellow crystalline powder.
Embodiment 1-1
[0075] The preparation of the intermediate of structure shown in formula (L2):
[0076]
[0077] In a 100mL round-bottomed flask, at 0°C, add 5.0mmol of 1-adamantanyl chloride and 25mL of anhydrous toluene in turn. After magnetically stirring to dissolve, add 10mmol of anhydrous potassium carbonate, and slowly add 2-methylaminopyridine 6.3 mmol, react under ice-bath conditions for 12 hours, filter, and obtain 1.154 g of light yellow crude product after removing the solvent by rotary evaporation under reduced pressure. The crude product was recrystallized from a mixed solvent of ethyl acetate and ether to obtain a white powder. Recrystallized in a mixed solvent of ethyl acetate and petroleum ether (v / v=1:3) to obtain 1.050 g of white powder with a yield of 76%. Its detection data are as follows.
[0078] The white powder was subjected to elemental analysis, and the result was C 17 h 22 N 2 O: C, 75.36%; N, 10.18%; H, 8.47%; Theoretical calculation value: C, 75.52%; N, 1...
PUM
Login to View More Abstract
Description
Claims
Application Information
Login to View More