Lenalidomide derivative preparation method and application
A technology of drugs and compounds, applied in the field of medicinal chemistry, can solve problems such as COX-1 ineffectiveness
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Embodiment 1
[0073] Example 1: Methyl 3-(4-amino-1-isoindolinone-2-yl)-3-(3-ethoxy-4-methoxyphenyl)propionate (compound 6)
[0074]
[0075] 1.1 Step 1. Preparation of (E)-2-((3-ethoxy-4-methoxybenzylidene)amino)-2-phenylacetamide (compound 2)
[0076] 3-Ethoxy-4methoxybenzaldehyde (compound 1, 31.0 g, 172 mmol) was dissolved in 200 mL of methanol, then 2-aminophenylacetamide (25.8 g, 172 mmol) was added, and stirred at room temperature for 18 hours. After the reaction, the reaction solution was concentrated and recrystallized from ethanol to obtain a white solid (E)-2-((3-ethoxy-4-methoxybenzylidene)amino)-2-phenylacetamide (23.6g, 44.0%). 1 H NMR(DMSO-d6,400MHz)δ8.74(s,1H),7.58-6.95(m,8H),5.36(s,1H),4.09(m,2H),3.83(s,3H),1.32( m,3H).ESI-MS m / z:313.4[M+H] + .
[0077] 1.2 Step 2, Preparation of methyl 3-((2-amino-2-oxo-1-phenylacetamido)-3-(3-ethoxy-4-methoxyphenyl)propionate (compound 3)
[0078] Dissolve (E)-2-((3-ethoxy-4-methoxybenzylidene)amino)-2-phenylacetamide (compound 2,...
Embodiment 2
[0085]Example 2: Methyl 3-(4-acetylamino-1-isoindolinone-2-yl)-3-(3-ethoxy-4-methoxyphenyl)propionate (Compound 7)
[0086]
[0087] Dissolve methyl 3-(4-amino-1-isoindolinon-2-yl)-3-(3-ethoxy-4-methoxyphenyl)propanoate (1.0 g, 2.6 mmol) In 10mL tetrahydrofuran, add dicyclohexylcarbodiimide (0.54g, 2.6mmol), 4-dimethylaminopyridine (0.32g, 2.6mmol), acetic acid (0.16g, 2.6mmol) to the reaction respectively, and stir at room temperature 10 hours. The reaction solution was filtered, concentrated under reduced pressure, and column chromatography gave white solid 3-(4-acetylamino-1-isoindolinone-2-yl)-3-(3-ethoxy-4-methoxybenzene base) methyl propionate (0.97 g, 88.2%). 1 H NMR(DMSO-d6,400MHz)δ7.65-6.74(m,6H),5.51(m,1H),4.22(S,2H),4.09(m,2H),3.83(s,3H),3.68( s,3H),2.92(m,2H),2.04(s,2H),1.32(m,3H).ESI-MS m / z:449.5[M+Na] + .
Embodiment 3
[0088] Example 3: Methyl 3-(1-oxo-4-pentanoylaminoisoindolinone-2-yl)-3-(3-ethoxy-4-methoxyphenyl)propionate (compound 8)
[0089]
[0090] Method is with embodiment 2, raw material is 3-(4-amino-1-isoindolinone-2-yl)-3-(3-ethoxy-4-methoxyphenyl) methyl propionate and Valeric acid to obtain white solid powder, yield: 92.5%. 1 H NMR(DMSO-d6,400MHz)δ7.65-6.74(m,6H),5.51(m,1H),4.22(S,2H),4.09(m,2H),3.83(s,3H),3.68( s,3H),2.92(m,2H),2.39(m,2H),1.63(m,2H),1.32(m,2H),0.90(m,3H).ESI-MS m / z:469.5[M +H] + .
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