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. Author manuscript; available in PMC: 2014 May 23.
Published in final edited form as: J Med Chem. 2013 May 13;56(10):4028–4043. doi: 10.1021/jm400241j

Scheme 7.

Scheme 7

Synthesis of amide derivative 36.

Reagents and conditions: (a) α-methyl benzyl amine, EDCI•HCl, DMF, 0 °C - rt, 12 h, 71%. An analogue of 22 in which the amide group is inverted was prepared using the method outlined in Scheme 7. Amide 36 was generated by coupling 2-(pyridin-4-yl)benzo[d]oxazole-5-carboxylic acid (35) and α-methylbenzylamine in the presence of EDCI•HCl.