1-methyl-7H-indene[1, 2-b]quinolinetrifluoromesylate-7-(4-dimethylamino) benzyl alkene derivant and preparation thereof
A technology of quinoline triflate and dimethylamino is applied in the field of antitumor drug preparation, can solve the problems of difficult substituents, complicated synthesis steps and the like, and achieves the effects of strong inhibitory effect, simple process and good yield
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Embodiment 1
[0028] Example 1: Preparation of 1-methyl-7-(4-dimethylaminobenzene)-7H-inden[1,2-b]quinoline trifluoromethanesulfonate
[0029] (1) Condensation cyclization: 1-indanone (0.46g, 3.5mmol) and anthranilic acid (0.28g, 2mmol) were heated and melted, refluxed at 180°C for 1.5h, and the reaction was terminated. After washing with pyridine and diethyl ether, a yellow solid (0.32 g, 67.6%) was obtained, m.p.360-365.
[0030] (2) Chlorine substitution: the yellow solid obtained in step (1) (0.32 g, 1.35 mmol) was dissolved in phosphorus oxychloride (5 mL), and refluxed at 110° C. for 4 h to complete the reaction. Phosphorus oxychloride was removed under reduced pressure, and saturated NaHCO 3 Adjust to neutral with CH 2 Cl 2 Extracted three times, washed with saturated brine, anhydrous Na 2 SO 4 Dry, filter and evaporate to dryness. Separation and purification by column chromatography, eluting with petroleum ether-ethyl acetate (50:1) gave a white solid (0.30 g, 88.2%), m.p.162-...
Embodiment 2
[0035] Example 2: Preparation of 1,3-dimethyl-7-(4-dimethylaminobenzene)-7H-indene[1,2-b]quinoline trifluoromethanesulfonate
[0036] (1)-(3) method is the same as embodiment one
[0037] (4) Methylation reaction: Dissolve 3-methyl-7H-indene[1,2-b]quinoline (0.21g, 0.9mmol) in 5mL of dry CH 2 Cl2 Medium, N 2 Methyl trifluoromethanesulfonate (0.21 mL, 1.8 mmol) was added under protection, stirred at room temperature for 24 h, and the reaction was tracked by TLC. After the reaction, evaporated to dryness, separated and purified by column chromatography, CH 2 Cl 2 -CH 3 Gradient elution with OH (100:1~50:1) afforded 1,3-dimethyl-7H-indene[1,2-b]quinoline triflate (0.33 g, 96%) as a white solid.
[0038] (5) Coupling reaction: 1,3-dimethyl-7H-inden[1,2-b]quinoline trifluoromethanesulfonate (0.33g, 0.87mmol) and p-dimethylaminobenzaldehyde (0.21 g, 1.30mmol) was refluxed in 50mL glacial acetic acid for 2 days. Distillation under reduced pressure, separation and purification ...
Embodiment 3
[0040] Example 3: Preparation of 1-methyl-3-fluoro-7-(4-dimethylaminobenzene)-7H-indene[1,2-b]quinoline trifluoromethanesulfonate
[0041] (1)-(3) method is the same as embodiment one
[0042] (4) Methylation reaction: Dissolve 3-fluoro-7H-inden[1,2-b]quinoline (0.21 g, 0.9 mmol) in 5 mL of dry CH 2 Cl 2 Medium, N 2 Methyl trifluoromethanesulfonate (0.21 mL, 1.8 mmol) was added under protection, stirred at room temperature for 28 h, and the reaction was tracked by TLC. After the reaction, evaporated to dryness, separated and purified by column chromatography, CH 2 Cl 2 -CH 3 OH (100:1~50:1) gradient elution gave white solid 1-methyl-3-fluoro-7H-indene[1,2-b]quinoline trifluoromethanesulfonate (0.31g, 91%) .
[0043] (5) Coupling reaction: 1,3-dimethyl-7H-inden[1,2-b]quinoline trifluoromethanesulfonate (0.31g, 0.82mmol) and p-dimethylaminobenzaldehyde (0.21 g, 1.30mmol) was refluxed in 50mL glacial acetic acid for 2 days. Distillation under reduced pressure, separation...
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