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. 2014 Nov 13;57(23):10013–10030. doi: 10.1021/jm501256y

Scheme 3. Synthesis of Inhibitors 16.

Scheme 3

Reagents and conditions: (a) CuI, trans-N,N-dimethylcyclohexane-1,2-diamine, Cs2CO3, DMF, 90 °C; (b) LiOH, THF/H2O (1:1), 100 °C; (c) 6-methylpyridin-3-amine, EDC, HOBt, DIEA, CH2Cl2, 25 °C; (d) Pd/C, MeOH, H2; (e) 1-chloro-2-isocyanatobenzene, CH2Cl2, 25 °C.