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. Author manuscript; available in PMC: 2021 Sep 9.
Published in final edited form as: J Med Chem. 2020 Nov 16;63(22):13951–13972. doi: 10.1021/acs.jmedchem.0c01498

Scheme 2. Synthetic Routes of Compound 12da.

Scheme 2.

aReagents and conditions: (a) NaH, DMF, 0 °C to rt., 2 h, and 73%. (b) (1) Con. HCl/AcOH/H2O, reflux, and overnight; (2) POCl3, reflux, 3 h, and 51% for two steps. (c) 6, Pd(OAc)2, XantPhos, Cs2CO3, 1,4-dioxane, 100 °C, overnight, and 56%. (d) (1) 2 N NaOH, MeOH, reflux, and 1 h; (2) 2 N HCl, rt., and 95%. (e) NH2CH2CH2OH, EDCI, DMAP, DMF, rt., overnight, and 83%.