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Synthesis of M4 PAM analogs 6, 16, 17. Reagents and conditions: (a) R-X, DCM, DIPEA, rt. (b) R-Het-X, Cs2CO3, DMF, heat (c) Ar-X, Pd2(dba)3, rac-BINAP, Cs2CO3, toluene, 100 °C (d) TFA, DCM, rt, 3 hr (e) 5-amino-3,4-dimethylthieno[2,3-c]pyridazine-6-carboxylic acid, HATU, DIPEA, DMF, 2 hr.
