A kind of 4,5-diazafluorene derivative and its preparation method and application
A technology of diazafluorene and derivatives is applied in the field of 4,5-diazafluorene derivatives and their preparation, which can solve the problem of not targeting human telomere G-quadruplex anti-tumor clinical drug reports, etc. quality, the effect of improving the reaction yield
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Embodiment 1
[0042] Preparation of Example 1 Compound 11c Its synthetic route is as follows:
[0043]
[0044] 1) Preparation of Intermediate 2c Dissolve p-bromoacetophenone (1.99g, 10.0mmol) in 25mL of absolute ethanol, add semicarbazide hydrochloride (1.23g, 11.0mmol) and anhydrous sodium acetate (0.90g, 11.0mmol) , reacted at 75°C for 6 hours, concentrated, cooled, precipitated a white solid, filtered, recrystallized with ethanol / water (4:1), filtered, washed with a small amount of water, dried to obtain 2.30 g of white solid 2c, yield 89.84% ;
[0045] 2) Preparation of Intermediate 4c Stir 15.5mL of DMF in an ice bath for ten minutes, slowly add 3.1mL of phosphorus oxychloride dropwise to it, keep the temperature below 5°C, stir for fifteen minutes, then add compound 2c (2.0 g, 7.8mmol), and kept stirring at the temperature for half an hour. Then slowly raise the temperature to 80° C., react for 5 hours, and detect by TLC until the reaction is complete. Pour the mixture into cru...
Embodiment 2
[0065] The preparation of embodiment 2 compound 8a
[0066] Compound 8a: 5-((3-(4-fluorophenyl)-1H-pyrazol-4-yl)methylene)-5H-cyclopenta[2,1-b:3,4-b']di Pyridine (8a)
[0067] (1) 8a chemical structural formula:
[0068]
[0069] (2) Chemical reaction steps:
[0070] The test method and steps are the same as 11c. After purification, a light yellow solid (8a) was obtained with a yield of 85%; m.p.217-219°C, purity: 98.1% (HPLC). Characterization data:
[0071] 1 H NMR (DMSO-d 6 ,500MHz,ppm):δ13.498(br.s,1H,N-H),8.680-8.668(dd,J=5.0,1.5Hz,1H,pyridine-H 8 ), 8.646-8.634 (dd, J=5.0, 1.5Hz, 1H, pyridine-H 2 ), 8.496-8.478 (dd, J=8.0, 1.5Hz, 1H, pyrazol-H 11 ), 8.227-8.212 (d, J=7.5Hz, 1H, pyridine-H 6 ),7.895(br.s,1H,C-H 10 ), 7.743-7.716 (dd, J=5.0, 1.5Hz, 2H, benzene-H), 7.480-7.455 (dd, J=5.0, 1.5Hz, 1H, pyridine-H 4 ),7.363-7.338(dd,J=5.0,1.5Hz,1H,benzene-H),7.302(m,3H,pyridine-H 3,7 and benzene-H).MS(ESI)calcd for C 21 h 13 FN 4 :340.11,found:341.1(M+H + )....
Embodiment 3
[0072] The preparation of embodiment 3 compound 8b
[0073] Compound 8b: 5-((3-(4-chlorophenyl)-1H-pyrazol-4-yl)methylene)-5H-cyclopenta[2,1-b:3,4-b']di Pyridine (8b)
[0074] (1) 8b chemical structural formula:
[0075]
[0076] (2) Chemical reaction steps:
[0077] The test method and steps are the same as 11c. After purification, a light yellow solid (8b) was obtained with a yield of 83%; m.p.242-244°C, purity: 97.8% (HPLC). Characterization data:
[0078] 1 H NMR (DMSO-d 6 ,500MHz,ppm):δ13.576(br.s,1H,N-H),8.682-8.674(d,J=4.0Hz,1H,pyridine-H 8 ), 8.646-8.638 (d, J=4.0Hz, 1H, pyridine-H 2 ), 8.506-8.491 (d, J=7.5Hz, 1H, pyrazol-H 11 ), 8.218-8.205 (d, J=6.5Hz, 1H, pyridine-H 6 ),7.905(br.s,1H,C-H 10 ), 7.722-7.707 (d, J=7.5Hz, 2H, benzene-H), 7.522 (br.s, 3H, pyridine-H 4 andbenzene-H), 7.484-7.459 (dd, J=7.5, 5.0Hz, 1H, pyridine-H 7 ), 7.363-7.338 (dd, J=7.5, 5.0Hz, 1H, pyridine-H 3 ).MS(ESI)calcd for C 21 h 13 ClN 4 :356.08,found:357.1(M+H + ).
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