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. 2023 Mar 28;14:1733. doi: 10.1038/s41467-023-37254-w

Fig. 4. Synthesis of compounds 2-15.

Fig. 4

Reaction conditions with yields in parentheses: I. Ac2O, AcOH, DCM, 55%; II. HATU, DIPEA, DCM (3, 83%; 4, 91%); III. N2H4•H2O, EtOH (5 and 6, 97%); IV. methyl (E)-4-chloro-4-oxobut-2-enoate, DIPEA, DCM for 7 (56%), and K2CO3, DMF for 8 (34%). Compounds 9 (50%), 10 (37%), 11 (56%), 12 (23%), and 13 (60%) were prepared with the corresponding acid chlorides under conditions described for step IV. Compounds 14 (89%) and 15 (83%) were prepared analogously to step II with 2-methylbenzoic acid and 5-acetamido-2-methylbenzoic acid, respectively.