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. Author manuscript; available in PMC: 2021 Apr 3.
Published in final edited form as: ChemMedChem. 2020 Feb 14;15(7):643–658. doi: 10.1002/cmdc.201900730

Scheme 2.

Scheme 2.

Route A: a) EDC hydrochloride, triethylamine, dry DCM; b) 4M HCl in dioxane, dry THF. Route B: c) N-methylpiperazine, dry potassium carbonate, dry DMF, 100 °C; d) H2, 10% Pd/C, MeOH; e) benzyl chloroformate, triethylamine, dry THF, 0 °C; f) trifluoracetic acid, dry DCM; g) PyBOP, triethylamine, dry DMF, N2; b) 4M HCl in dioxane, dry THF. Route C: h) phenol or thiophenol, dry potassium carbonate, dry DMF, 100 °C; i) H2, 10% Pd/C, EtOH; j) benzyl chloroformate, dry potassium carbonate, THF/H2O = 1:1, 0 °C; f) trifluoracetic acid, dry DCM; g) PyBOP, triethylamine, dry DMF, N2; b) 4M HCl in 1,4-dioxane, dry THF. Route D: j) benzyl chloroformate, dry potassium carbonate, THF/H2O = 1:1, 0 °C; a) EDC hydrochloride, triethylamine, dry DCM; b) 4M HCl in 1,4-dioxane, dry THF. Route E: k) benzoyl chloride, triethylamine, dry DCM; l) N-phenyl- or N-benzyl-2-bromoacetamide, dry potassium carbonate, dry CH3CN, 70 °C; m) 2N LiOH, dry THF, g) PyBOP, triethylamine, dry DMF, N2; b) 4M HCl in 1,4-dioxane, dry THF..