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2.1 Amide-Bond-Forming Reactions

DOI: 10.1055/sos-SD-241-00002

Li, Y.; Fang, X.; Wang, Y.Science of Synthesis: DNA Encoded Librariesearly view.

General Introduction

Amide-bond-forming reactions are involved in at least one step in the preparation of most DNA-encoded chemical libraries (DELs) because of the versatility and DNA compatibility of these reactions. Amidation is typically achieved through the condensation of amines and carboxylic acids (Scheme 1), which are two of the largest commercially available building-block pools because of their widespread use in medicinal chemistry for the synthesis of drug-like screening libraries. Commonly used reagents for the coupling of amines and carboxylic acids in DEL transformations are N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide (EDC), N,N′-diisopropylcarbodiimide (DIC), N,N′-dicyclohexylcarbodiimide (DCC), N-[(dimethylamino)(1H-1,2,3-triazolo[4,5-b]pyridin-1-yl)methylene]-N-methylmethanaminium hexafluorophosphate 3-oxide (HATU), 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMTMM), and 3-[(diethoxyphosphoryl)oxy]-1,2,3-benzotriazin-4(3H)-one (DEPBT) (Scheme 2).

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