For the enumeration of potential compounds, we utilized the KNIME Analytics Platform , leveraging its capabilities for integrating and automating cheminformatics processes . Our approach focused on two key synthetic reactions: O-alkylation and amide coupling. We generated the reaction SMARTS for the two reactions and, using the RDKit two-component reaction node within KNIME, systematically generated a virtual library of compounds. This process was based on the chemotype we had previously identified, employing Enamine's building blocks to explore various compound permutations. The enumeration process yielded approximately 200,000 virtual compounds, thereby expanding our chemical space and facilitating the discovery of novel variants related to our target chemotype. This expansive virtual library serves as a resource for subsequent screening and experimental validation.