Abstract
A library of 24 6-(5-oxo-1-phenylpyrrolidin-3-yl)pyrimidine-5-carboxamides 10{1,2; 1–12} was prepared by a parallel solution-phase approach. The synthesis comprises a five-step transformation of itaconic acid (11) into 1-methyl and 1-phenyl substituted 6-(5-oxo-1-phenylpyrrolidin-3-yl)pyrimidine-5-carboxylic acids 17{1,2} followed by parallel amidation of 17{1,2} with a series of 12 aliphatic amines 18{1–12} to afford the corresponding carboxamides 10 in good overall yields and in 80–100% purity.
Highlights
10{1,2; 1–12} was prepared by a parallel solution-phase approach
A part of our research in this field has been focused on the synthesis of aminoethyl functionalized heterocycles
Transformation of 12 into the enaminone 14 as the first key intermediate was performed following the literature protocol [23]: Masamune-Claisen condensation of 12 with 1,1'-carbonyldiimidazole (CDI) as activating agent in anhydrous acetonitrile at room temperature gave the β-keto ester 13, which when treated with N,N-dimethylformamide dimethylacetal (DMFDMA) in refluxing toluene gave the enaminone intermediate 14
Summary
2-[(Hetero)aryl]ethylamines, such as dopamine, histamine, tryptamine, serotonin, and melatonin are representative chemical messengers playing a crucial role in biological processes [1]. The preparation of libraries of their novel synthetic analogues is of particular interest and represents an important target in medicinal [2,3,4,5], synthetic organic, and combinatorial chemistry [6,7,8,9,10]. A part of our research in this field has been focused on the synthesis of aminoethyl functionalized heterocycles. In this context, we first reported the synthesis. We have focused our attention on 2-substituted 6(5-oxo-1-phenylpyrrolidin-3-yl)pyrimidine-5-carboxamides 10 (Figure 1). We report a parallel solution-phase synthesis of a library of 24 6-(5-oxo-1-phenylpyrrolidin3-yl)pyrimidine-5-carboxamides 10{1,2; 1–12} as novel 2-heteroarylethylamine derivatives
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