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. Author manuscript; available in PMC: 2023 Feb 24.
Published in final edited form as: J Med Chem. 2022 Feb 4;65(4):3644–3666. doi: 10.1021/acs.jmedchem.1c02165

Scheme 1. Synthesis of Key Intermediate 2a.

Scheme 1.

aReaction conditions: (a) Boc2O, NEt3, rt, 2 h; (b) PPh3, I2, imidazole, DCM, 4 h; (c) Benzyl piperazine-1-carboxylate (46), K2CO3, CH3CN, 80 °C, overnight; (d) TFA/DCM, rt, 30 min; (e) 4-[(tert-butoxycarbonyl)amino]-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxylic acid (48), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCI), 1-hydroxy-7-azabenzo-triazole (HOAt), N-methylmorpholine (NMM), dimethyl sulfoxide (DMSO), rt; and (f) Pd/C, H2, MeOH, rt.