Aromatic hydrazine compound, and preparation method and applications thereof

[0039] Example 1

[0040] Add 564mg EDCI (2.94mmol), 64mg DMAP (0.52mmol), 728μL TEA (5.33mmol), 556mg 4-methoxyphenylhydrazine hydrochloride (3.19mmol) into the reaction flask, add 400mg 3,5- Dimethyl benzoic acid (2.66 mmol) was reacted at room temperature for 8 hours. TLC detected that the reaction was complete. The THF was spun off, extracted with ethyl acetate 3 times, washed with saturated sodium chloride, dried and concentrated to obtain a crude product. Purified by column chromatography (PE:EA=10:1→PE:EA=5:1), 351 mg of pale yellow solid was obtained, with a yield of 48.6%. The light yellow solid nuclear magnetic detection, 1HNMR (400MHz, DMSO) δ 8.127 (s, 1H), 7.447 (s, 1H), 7.198 (s, 1H), 6.922-6.892 (m, 2H), 6.841-6.811 (m , 2H), 3.772 (s, 3H), 2.379 (s, 6H) ppm. The synthesis equation of Example 1 is as follows:

[0041]

[0042] Example 2

[0043] 200mg Al (0.994mmol) of compound was dissolved in 2mL DMF, 209.9mg EDCI (1.09mmol) and 159.7mg HOBt (1.09mmol) were added under stirring at room temperature, 117.6μL phenylhydrazine (1.19mmol) was slowly added dropwise, and the reaction was complete in 6h at room temperature. The reaction solution was added with water, extracted with ethyl acetate for 3 times, washed with saturated brine, dried and concentrated to obtain a crude product of compound 3, which was recrystallized to obtain a white solid product of 230 mg, with a yield of 79.4%. 1HNMR(400MHz,DMSO)δ10.547(d,J=2.6Hz,1H), 8.079(d,J=8.28Hz,2H),8.001,(d,J=2.52Hz,1H),7.949(d,J =8.24Hz,2H),7.538(s,2H),7.177(t,J=15.44Hz,2H),6.815(d,J=8.12Hz,2H),6.748(t,J=14.32Hz,1H)ppm .13CNMR (101MHz, DMSO) δ 165.91, 149.72, 147.11, 136.46, 129.27, 128.53, 126.27, 119.28, 112.83 ppm. The synthesis equation of Example 2 is as follows:

[0044]

[0045] Example 3

[0046] 500 mg compound A2 (2.99 mmol) was dissolved in 3 mL DMF, 631.49 mg EDCI (3.289 mmol) and 480.194 mg HOBt (3.289 mmol) were added under stirring at room temperature, 353.89 μL phenylhydrazine (3.59 mmol) was slowly added dropwise, and the reaction was complete in 6 hours at room temperature. The reaction solution was added with water, extracted with ethyl acetate 3 times, washed with saturated brine, dried and concentrated to obtain crude compound 4, which was recrystallized to obtain 246.9 mg of yellow solid product, with a yield of 32.09%. 1HNMR(400MHz,DMSO)δ10.443(d,J=2.48Hz,1H),8.114(m,1H),8.058(d,J=2.52Hz,1H),7.875(m,1H),7.773(m, 2H) 7.197 (m, 2H), 6.880 (d, J = 7.67 Hz, 2H), 6.759, (t, J = 14.48 Hz, 1H) ppm. 13CNMR (101MHz, DMSO) δ 165.90, 149.47, 147.69, 134.30, 131.75 ,131.40,129.91,129.23,124.81,119.23,112.78ppm. The synthesis equation of Example 3 is as follows:

[0047]