We hypothesized that the nucleophilicity of the amine partner could affect yields in the amide coupling of 1 (i.e., less nucleophilic amines could deliver the respective amide products in lower yields than more nucleophilic ones). Therefore, the EDC-mediated reaction of 1 with more nucleophilic N-Boc piperazine and weakly nucleophilic ethyl Tolerance of a free hydroxyl group in the amine partner was tested by reacting benzoic acid and (4-(aminomethyl)phenyl)methanol (Scheme 2, b). Selective acylation of the amino group was achieved affording amide 12 with a yield of 85%, but no ester isomer of 12 was formed. This outcome agrees with the analogous reactions in solution and those by mechanochemistry. Next, we explored the use of hydroxyl groupcontaining amino acids, namely N-Boc-L-serine and N-Boc-L-tyrosine, in the reaction with aniline (8) and L-phenylalanine methyl ester (Scheme 2, c). Aromatic amides 13 and 15 were prepared with high yields (82% and 90% yields, respectively) in the reactions with 8. However, column chromatography purification was needed in these cases to The first synthetic route of imatinib was patented in 1993 by Zimmermann, followed by several improved protocols, including flow-based approaches and microwave-assisted solidphase synthesis. However, mechanochemical preparations have not been reported yet.