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. Author manuscript; available in PMC: 2013 Apr 12.
Published in final edited form as: J Med Chem. 2012 Mar 20;55(7):3088–3100. doi: 10.1021/jm2015183

Scheme 4.

Scheme 4

Synthesis of the Carbamoylsalicylamide 16 and the Urea 19

Reagents and conditions: (a) BnBr, K2CO3, acetone, reflux, 16 h; (b) 1) (COCl)2, CH2Cl2, room temp to 50 °C, 3 h; 2) 4-ethylaniline, MeCN, room temp, 18 h; (c) 10% Pd/C, H2, MeOH, room temp, 24 h; (d) 4-ethylaniline, CH2Cl2, room temp, 19 h; (e) BBr3, CH2Cl2, −78 °C to 0 °C.