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. Author manuscript; available in PMC: 2016 Jun 10.
Published in final edited form as: J Med Chem. 2015 Aug 4;58(15):5863–5888. doi: 10.1021/acs.jmedchem.5b00423

Scheme 9a.

Scheme 9a

aReagents and conditions: (a) (i) methyl 2-chloropyrazine-6-carboxylate or methyl 3-chloropyridazine-5-carboxylate or methyl 2-chloro-5-methylthiazole-4-carboxylate, Et3N or i-Pr2NEt, DMF, 60 °C, 16 h or i-Pr2NEt, DMSO, 110 °C, 24 h; (ii) LiOH·H2O, THF, CH3OH, H2O, rt, 30 min-16 h; (iii) 2 N aq HCl.