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. 2014 Aug 14;57(17):7355–7366. doi: 10.1021/jm500764v

Scheme 3. Synthesis of Analogues Based on PAT Template.

Scheme 3

Reagents and conditions: (a) BrCN, Et2O/hexane; (b) CH3SO3H, EtOH, reflux, 24 h; (c) (1) 6 M HCl, (2) NaOH 25% conc.; (d) PhSO2Cl, Et3N; (e) −78 °C, t-BuLi, 3,4,5-trimethoxybenzoyl chloride; (f) Boc2O, NaOH; (g) (chloromethanetriyl)tribenzene, Et3N, CH2Cl2; (h) HCl; (i) H2, Pd–C, 5%, EtOH, 40 psi; (j) PhCOSCN, Me2CO; (k) MeOH, 1 N NaOH; (l) EtOH, 65 °C; (m) NaOH, MeOH; (n) HBTU, NMM, HNCH3OCH3·HCl, CH2Cl2; (o) 3,4,5-trimethoxyphenylbromide, n-BuLi, THF.