Diaryl amide compound containing benzimidazole group as well as synthesis and application of diaryl amide compound
A technology of benzimidazolyl and arylamide, applied in the field of chemical medicine
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Embodiment 1
[0052] Synthesis of 2-chloro-N-[4-chloro-3-(1H-benzimidazol-2-yl)phenyl]-4-thiamphenicol benzamide (Ⅰ-1)
[0053] ①Add 2.98mmol of compound ⅰ-1, 2.98mmol of o-phenylenediamine (compound ⅱ-1), 3.28mmol of HBTU, 5.96mmol of triethylamine and 20mL of THF into a 50mL pear-shaped flask, stir at room temperature for 5h under nitrogen protection, and react After adding 40 mL of water to the solution, CH 2 Cl 2 Extract three times, 30mL each time, combine the organic phases, wash with 30mL of water, wash with 30mL of saturated brine, dry over anhydrous sodium sulfate, and distill under reduced pressure to obtain the crude product, the crude product is purified on a silica gel column, and the mobile phase is petroleum ether: ethyl acetate: triethylamine = 1:1:0.005, 714 mg of product was obtained with a yield of 82%. ESI-MS:m / z292.05[M+H] + .
[0054]
[0055] ②Add 1.714mmol of the product obtained in step ① (compound Ⅲ-1) and 12mL HOAc in a 25mL pear-shaped bottle, stir and ref...
Embodiment 2
[0062] Synthesis of 2-chloro-N-[4-chloro-3-(1-methyl-1H-benzimidazol-2-yl)phenyl]-4-thiamphenicol benzamide (Ⅰ-2)
[0063] ①Add 2.98mmol of compound ⅰ-1, 2.98mmol of o-phenylenediamine (compound ⅱ-1), 3.28mmol of HBTU, 5.96mmol of triethylamine and 20mL of THF into a 50mL pear-shaped flask, stir at room temperature for 5h under nitrogen protection, and react After adding 40 mL of water to the solution, CH 2 Cl 2 Extract three times, 30mL each time, combine the organic phases, wash with 30mL of water, wash with 30mL of saturated brine, dry over anhydrous sodium sulfate, and distill under reduced pressure to obtain the crude product, the crude product is purified on a silica gel column, and the mobile phase is petroleum ether: ethyl acetate: triethylamine = 1:1:0.005, 714 mg of product was obtained with a yield of 82%. ESI-MS:m / z292.05[M+H] + .
[0064]
[0065] ②Add 1.714mmol of the product obtained in step ① (compound Ⅲ-1) and 12mL HOAc in a 25mL pear-shaped bottle, sti...
Embodiment 3
[0074] 2-Chloro-N-[4-chloro-3-(4,7-dimethoxy-1H-benzimidazol-2-yl)phenyl]-4-thiamphenicol benzamide (Ⅰ-3) Synthesis
[0075] The difference with embodiment 1 is:
[0076] The o-phenylenediamine of step ① in embodiment 1 is replaced by 3,6-dimethoxy o-phenylenediamine;
[0077] Compound I-3. 1 H NMR (400MHz, CDCl 3 )δ10.90(1H,s),8.66-8.53(2H,m),7.61-7.52(2H,m),7.31(1H,d,J=7.9Hz),7.18(1H,d,J=7.9Hz ), 6.45(2H,s), 3.84(6H,s), 2.89(3H,s); ESI-MS: m / z520.03[M+H] + .
[0078]
PUM

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