Inhibitor of t790m mutant egfr and its application in the preparation of antitumor drugs
A technology of anti-tumor drugs and inhibitors, which is applied in the field of drugs for the treatment of tumors, and can solve the problems of poor selectivity, hindering the combination of inhibitors and ATP binding regions, and reducing the affinity of inhibitors and EGFR
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Embodiment 1
[0090] Example 1, (R)-N-(3-(1-((2-((4-(4-acetylpiperazin-1-yl)-2-methoxyphenyl)amino)-5-tri Fluoromethylpyrimidin-4-yl)oxy)ethyl)propyl)acrylamide
[0091]
[0092] Synthetic steps:
[0093]
[0094] Step 1: Preparation of tert-butyl 3-acetylphenylcarbamate (compound 2)
[0095] To a solution of 1-(3-aminophenyl)ethanone (compound 1) (8.0 g, 59.3 mmol) in dioxane (100 mL) was added (Boc) 2 O (16.8 g, 77.1 mmol). The obtained reaction solution was reacted at 150° C. for 4 hours, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (PE:EA=8:1 to 4:1) to obtain the target product (12.4 g, 88.6% yield) as a white solid. 1 H NMR (400MHz, CDCl 3 )δ7.95(s,1H),7.66(d,J=7.6Hz,1H),7.60(d,J=7.8Hz,1H),7.37(t,J=7.9Hz,1H),6.88(s, 1H), 2.59(s, 3H), 1.52(s, 9H).
[0096] Step 2: Preparation of tert-butyl (R)-(3-(1-hydroxyethyl)phenyl)carbamate (Compound 3)
[0097] (+)-DIP-Cl (5.5 g, 17.0 mmol) was dissolved in anhydrous THF...
Embodiment 2
[0104] Example 2, (S)-N-(3-(1-((2-((4-(4-acetylpiperazin-1-yl)-2-methoxyphenyl)amino)-5-tri Fluoromethylpyrimidin-4-yl)oxy)ethyl)propyl)acrylamide
[0105]
[0106] The synthetic method is as embodiment 1,
[0107] 1 H NMR (400MHz, CDCl 3 )δ8.34(s,1H),7.86(m,2H),7.57(m,3H),7.30(t,J=7.8Hz,1H),7.16(d,J=7.4Hz,1H),6.64– 6.37(m,3H),6.28(m,2H),5.78(d,J=10.3Hz,1H),3.87(s,3H),3.80–3.70(m,2H),3.69–3.54(m,2H) ,3.22–2.98(m,4H),2.19(s,3H),1.66(d,J=6.6Hz,3H).LC-MS:m / z 585(M+H) + .
Embodiment 3
[0108] Example 3, N-(3-(1-((2-((4-(4-acetylpiperazin-1-yl)-2-methoxyphenyl)amino)-5-trifluoromethylpyrimidine -4-yl)oxy)ethyl)propyl)acrylamide
[0109]
[0110] The synthetic method is as embodiment 1,
[0111] 1 H NMR (400MHz, CDCl 3 )δ8.34(s,1H),7.85(m,2H),7.48(m,3H),7.31(t,J=7.8Hz,1H),7.16(d,J=7.6Hz,1H),6.64– 6.37(m,3H),6.27(m,2H),5.79(d,J=10.2Hz,1H),3.86(s,3H),3.82–3.70(m,2H),3.68–3.58(m,2H) ,3.25–2.91(m,4H),2.06(s,3H),1.66(d,J=6.5Hz,3H).LC-MS:m / z 585(M+H) + .
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