A substituted pyrazolo[1,5-a]pyrimidine compound and its preparation method and application
A compound, 5-a technology, used in drug combinations, organic chemistry, pharmaceutical formulations, etc.
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Embodiment 1
[0092]
[0093] Step 1: Synthesis of ethyl 4-phenyl-2,4-dioxobutanoate
[0094]
[0095] Metal sodium particles (11.5 g, 0.50 mol) were added in batches to 400 mL of cooled ethanol, and the reaction was stirred until the sodium particles disappeared, and then warmed to room temperature. Diethyl oxalate (36.5 g, 0.25 mol) and acetophenone (30.0 g, 0.25 mol) were added to the above solution, and the temperature was raised to 70° C., stirred for 5 h, most of the ethanol was removed by evaporation under reduced pressure, and the residue was added to 500 mL of water. . Ethyl acetate was extracted twice, 200 mL each time, and the ethyl acetate phase was discarded. The aqueous phase was adjusted to pH 4 with concentrated hydrochloric acid, extracted three times with ethyl acetate, 150 mL each time, combined the ethyl acetate phases, washed with water three times, 200 mL each time, and the organic phase was dried over anhydrous sodium sulfate and evaporated under reduced pressu...
Embodiment 2
[0131]
[0132] 1 H NMR (400MHz, CDCl 3 )δ9.94(s, 1H), 8.50(d, J=5.2Hz, 1H), 8.31(d, J=2.2Hz, 1H), 8.21(dd, J=8.6, 5.3Hz, 2H), 8.02( dd,J=11.9,2.0Hz,1H),7.90(s,1H),7.64–7.50(m,2H),7.44(s,1H),7.34–7.27(m,3H),6.94(d,J= 2.2Hz, 1H), 6.44(d, J=5.1Hz, 1H), 4.28(t, J=6.6Hz, 2H), 4.04(s, 3H), 3.78–3.66(m, 4H), 2.58(t, J=7.1Hz, 2H), 2.48(s, 4H), 2.25–2.01(m, 2H); MS(ESI) m / z(%): 667.2[M+H] + .
[0133] Example 3: N-{3-fluoro-4-[6-methoxy-7-(3-morpholine propoxy)quinoline-4-oxyl]phenyl}-7-(2-fluorobenzene base) pyrazolo[1,5-a]pyrimidine-5-carboxamide (compound 3)
Embodiment 3
[0134]
[0135] 1 H NMR (400MHz, CDCl 3 )δ9.91(s,1H),8.48(d,J=5.3Hz,1H),8.27(d,J=2.4Hz,1H),8.00(dd,J=11.9,2.4Hz,1H),7.88( s,1H),7.83–7.75(m,1H),7.66–7.47(m,3H),7.42(s,1H),7.40–7.25(m,3H),6.93 (d,J=2.4Hz,1H) ,6.43(d,J=4.9Hz,1H),4.26(t,J=6.7Hz,2H),4.02(s,3H),3.78–3.61(m,4H),2.60– 2.40(m,6H), 2.19–2.05(m,2H); MS(ESI)m / z(%):667.7[M+H] + .
[0136] Example 4: N-{3-fluoro-4-[6-methoxy-7-(3-morpholine propoxy)quinoline-4-oxyl]phenyl}-7-(4-trifluoro Synthesis of Methylphenyl)pyrazolo[1,5-a]pyrimidine-5-carboxamide (Compound 4)
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