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Synthesis of PROTAC-Biguanide compounds based on the CRBN or the VHL ligand. (i) HATU, DIPEA, DMF, r.t, 5–12 h, (11: 34%; 12: 6%; 29: 7%); (ii) CuI, Na-L-Ascorbate, DMF, r.t, 3–16 h (16: 13%; 20: 14%; 32: 29%). (* denotes a chiral center and the fact that the compound was used as a racemic mixture).
