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. Author manuscript; available in PMC: 2022 Jun 4.
Published in final edited form as: J Med Chem. 2022 Feb 15;65(4):3404–3419. doi: 10.1021/acs.jmedchem.1c01934

Scheme 4. Synthetic Route for 29-31.

Scheme 4.

Reagents and conditions: a) (R)-piperidine-3-carboxylic acid, Na2CO3, THF, H2O, rt, 98%; b) 4,4-difluoropiperidine, HATU, DIEA, DMF, rt, 32%; c) dimethylphosphine oxide or diethylphosphine oxide, Pd(OAc)2, XantPhos, K3PO4, DMF, 120 °C, 88-95%; d) i. LiOH, THF, H2O, rt; ii. 4,4-difluoropiperidine, HATU, DIEA, DMF, rt, 83-95%.