A class of o-formamidobenzamide derivatives containing sulfone (sulfur) imine and its preparation method and use
A technology of o-formamidobenzamide and derivatives, which is applied in the field of o-formamidobenzamide derivatives, and can solve the problems of no activity exceeding the activity of the target molecular parent and the like
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Embodiment 1
[0063] Synthesis of 2-amino-3-methyl-5-cyanobenzoic acid III:
[0064] (1) Synthesis of 2-amino-3-methyl-5-iodobenzoic acid XI:
[0065]
[0066] In a 100 ml round-bottomed flask, add 3.0 g or 20 mmol of 2-amino-3-methyl-benzoic acid X, 30 ml of DMF, 6.7 g or 30 mmol of NIS, reflux and stir for 3 hours, then pour the reaction solution into In ice water, acidify with dilute hydrochloric acid to pH=6, filter, and wash the obtained solid with a small amount of ethanol to obtain 4.6 g of gray solid 2-amino-3-methyl-5-iodobenzoic acid XI, with a yield of 83%. 1 H NMR (400MHz, DMSO-d 6 ): δ: 7.88(s, 1H), 7.45(s, 1H), 2.08(s, 3H).
[0067] (2) Synthesis of 2-amino-3-methyl-5-cyanobenzoic acid III:
[0068]
[0069] Add 2.77 g or 10.0 mmol of 2-amino-3-methyl-5-iodobenzoic acid XI, 25 ml of DMF, and 1.34 g or 15 mmol of cuprous cyanide successively into a 100 ml round bottom flask, and stir at 145 degrees Celsius 4 hours. After the reaction was monitored by TLC, most of the...
Embodiment 2
[0071] 3-Halo-1-(3-chloropyridin-2-yl)-N-(4-cyano-2-methyl-6-((2-(methylthio)alkyl)carbamoyl)benzene base)-1H-pyrazole-5-carboxamide preparation
[0072] (1) Synthesis of 3-chloro-2-hydrazinopyridine VI:
[0073]
[0074] Add 50 mmoles of 2,3-pyridine V, 100 mmoles of hydrazine hydrate, and 50 ml of ethanol into a 100 ml three-necked round-bottomed flask, heat and reflux at 80 degrees Celsius for 20 hours, evaporate the solvent under reduced pressure, and weigh the obtained solid with ethanol Crystallization gave 6.5 g of needle-like crystals of 3-chloro-2-hydrazinopyridine VI, with a yield of 90%.
[0075] (2) Synthesis of ethyl 5-oxo-2-(3-chloropyridin-2-yl)pyrazoline-3-carboxylate VII:
[0076]
[0077] Add 100 ml of absolute ethanol to a 250 ml single-necked round-bottom flask, add 1.77 g or 55 mmol of sodium metal in batches, the temperature rises slightly, and form a homogeneous transparent solution after stirring for 10 minutes; add 7.1 g or 50 mmol of 3-chloro ...
Embodiment 3
[0094] 1-(3-Chloropyridin-2-yl)-3-halo-1H-pyrazole-5-formyl-2-methyl-4-cyano-6-(2-((N-cyanomethyl Synthesis of (sulfimino)alkyl)carbamoyl)aniline IB
[0095]
[0096] In a 50 ml three-neck round bottom flask, add 0.53 g, that is, 1.0 mmol 3-halo-1-(3-chloropyridin-2-yl)-N-(4-cyano-2-methyl-6-(2 -(methylthioalkyl)carbamoyl)phenyl)-1H-pyrazole-5-carboxamide IA was added to 30 ml of dry tetrahydrofuran, stirred, and cooled to 0°C in an ice-water bath. Then add 0.16 g, 4 mmol cyanamide and 0.33 g, 1.0 mmol iodobenzene acetate respectively, stir at this temperature for 3 hours, then stir overnight at room temperature, the next day, the reaction solution is directly decompressed to remove the solvent, and the residue is subjected to 200~ Purified by 300 mesh silica gel column chromatography to obtain white solid 1-(3-chloropyridin-2-yl)-3-halo-1H-pyrazole-5-formyl-2-methyl-4-cyano-6- (2-((N-cyanomethylsulfimino)alkyl)carbamoyl)aniline IB, the eluent is ethyl acetate, and the ph...
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