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. Author manuscript; available in PMC: 2014 Sep 1.
Published in final edited form as: Eur J Med Chem. 2013 Jun 29;67:196–207. doi: 10.1016/j.ejmech.2013.06.041

Scheme 1.

Scheme 1

a) i. K2CO3, Cu, Cu2O, 2-ethoxyethanol, N2, 130 °C, 24 h, 67%; ii. DMF-DMA in toluene, reflux, 2 h, 85%; b) i. Cs2CO3, Pd(OAc)2, X-Phos, Celite, toluene/t-BuOH, N2, mw, 120-150 °C, 30-60 min, 74% for 2b and 2c; c) Cs2CO3, Pd(OAc)2, BINAP, toluene, N2, reflux 12 h, 64% for 2d; d) MeI/NaH (60% oil suspension), 0 °C, 1 h; e) LiAlH4/THF, 0 °C, 1 h, 97%; f) 30% NH2Me/MeOH, 100-120 °C, mw, 1-2 h for 3d, 4d-f; g) MeOH/THF, 3N NaOH aq, reflux, 5 h, 90% for 4h; h) EDCI, HOBt, cyclopropylamine or cyclopentylamine, CH2Cl2, rt, 24 h for 4i and 4j.