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. 2014 Sep 17;57(19):8099–8110. doi: 10.1021/jm5010495

Scheme 1. Synthesis of Analogues 153 and 7175.

Scheme 1

Reagents and conditions: (a) 2-(trifluoromethyl)benzoic acid, EDC (1.2 equiv), HOBt (1.2 equiv), Et3N (3.0 equiv), CH2Cl2, 72 h; (b) 5% NaOH, reflux 3 h; (c) N,N-dimethylaniline, POCl3, toluene, reflux 1 h; (d) RNH2, i-Pr2NEt, DMF, 18 h, 60 °C; (e) for analogue 1, [thiophen-2-ylmethanamine]; for analogues 2253 and 7175, [(4-(pyridin-3-yl)phenyl)methanamine], Et3N, CHCl3, 18 h, 60 °C; (f) for analogues 2233, 3753, and 71–75, R′B(OH)2 (3 equiv), 2 M Na2CO3 (4 equiv), DPP-Pd silica bound (0.3 equiv), or Pd(PPh3)4 (0.2 equiv), DME, MW, 150 °C, 30–45 min; (g) for analogues 3436, R′NH2 (3.0 equiv), THF, sealed tube 100 °C, 24 h.

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