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. Author manuscript; available in PMC: 2018 Nov 22.
Published in final edited form as: J Med Chem. 2017 Nov 9;60(22):9184–9204. doi: 10.1021/acs.jmedchem.7b00941

Scheme 4. Synthesis of 43–45a.

Scheme 4

aReagents and conditions: (a) ethyl 2-bromothiazole-4-carboxylate, K2CO3, 120 °C, 3–4 h, 27–78% (b) bis(pinacolato)diboron, PdCl2(dppf), AcOK, 1,4-dioxane, 95 °C, overnight 49 % (c) 4-(bromomethyl)benzenesulfonamide, 2N Na2CO3 (aq), Pd(Ph3P)4, tolune/EtOH (3/1), 80 °C, 2 h 64–95% (d) 1.5N LiOH (aq), THF, 2h (e) 4-hydroxybenzenesulfonamide, K2CO3, acetone, 20 h, 92% (f) 1,1-dimethoxy-N,N-dimethylmethanamine, 90 °C, overnight, then N2H4, EtOH, 60 °C, 4 h, 27%.