Preparation of HIF-2alpha small-molecule inhibitor and application thereof
A small molecule inhibitor, HIF-2 technology, applied in the field of medicine to achieve the effects of reduced toxicity, broad anti-cancer spectrum and good inhibitory effect
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Embodiment 1
[0099] Example 1 1-([1,2,4]Triazolo[4,3-a]pyrazin-8-yl)-N-benzyl-N-(furan-2-ylmethyl)methanamine ( Preparation of A1).
[0100] Step 1. Dissolve 3-bromo-2-chloropyrimidine (10g, 0.052mol) in toluene (200ml), cool down to -65°C, add DMF (dimethylformamide) (6.2ml, 0.08mol) dropwise , After dropping, n-butyllithium (1.57M solution in n-hexane; 51 mL, 0.08 mol) was added dropwise. After stirring for 20 minutes, the reaction was terminated with 1N hydrochloric acid, then the reaction solution was extracted with ethyl acetate, several layers were washed with water, dried over anhydrous magnesium sulfate, filtered, and concentrated to dryness to obtain the product (intermediate a) without further purification. in the next step.
[0101] Step 2. Sodium borohydride (2 g, 0.052 mol) was slowly added in batches to the solution of intermediate a dissolved in ethanol (30 mL) at room temperature, and stirred for 30 minutes after the addition. After quenching the reaction with 36% glacia...
Embodiment 2
[0107] Example 2 1-([1,2,4]Triazolo[4,3-a]pyrazin-8-yl)-N-(4-fluorobenzyl)-N-(furan-2-ylmethane yl) methylamine (A2).
[0108] The preparation method is the same as that of Example 1, ESI-MS m / z: 337.36; 1 H-NMR (400MHz, DMSO-d 6 )δ9.13(s,1H),8.36(d,J=2.7Hz,1H),7.68(d,J=2.7Hz,1H),7.44(dd,J=0.32Hz,2H),7.36(d, J=4.3Hz, 1H), 7.07(t, 2H), 6.52(d, J=0.88Hz, 1H), 6.30(t, J=0.88Hz, J=4.3Hz, 1H), 3.99(s, 2H) , 3.82(s, 2H), 3.54(s, 2H).
Embodiment 3
[0109] Example 3 1-([1,2,4]Triazolo[4,3-a]pyrazin-8-yl)-N-(3-bromophenyl)-N-(furan-2-ylmethane yl) methylamine (A3).
[0110] The preparation method is the same as that of Example 1, ESI-MS m / z: 398.26.
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