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. 2017 Mar 24;22(4):522. doi: 10.3390/molecules22040522

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© 2017 by the authors.

Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).

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Scheme 2 — Synthesis of key building blocks 6 and 7 as well as inhibitors 10b–i (series 1), 11a–e (series 2), 12a–g (series 3), and 16a–b (series 4). Reagents and Conditions: (i) NaHMDS, THF, 2 h 0 °C, 1 h r.t.; (ii) CH₃CHOOH, NaNO₂, 1 h 0 °C, 3.5 h r.t.; (iii) H₂, Pd/C, HCl-saturated 2-propanol, 12 h r.t.; (iv) methyl thiocyanate, DMF, 45 min reflux, 45 min r.t.; (v) NH₃, 20–30 bar, 18 h 180 °C; (vi) HNR₂, 12 h 160 °C; (vii) carboxylic acid, CDI or PyBOP/DIPEA, DMF, 12 h 110 °C; (viii) isocyanate, DIPEA, DMF, 12 h r.t.