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. 2018 Oct 19;3(10):13647–13666. doi: 10.1021/acsomega.8b01481

Scheme 7. General Synthetic Route of TRH Mimetics Including l-Histidine as the Middle-Part Fragment.

Scheme 7

Reagents and conditions: (a) (1) aq. HCl, NaNO2, H2O, 0 °C; (2) K2CO3, H2O, 0 °C to rt or (1) HCl in 1,4-dioxane, isoamyl nitrite, DMF, −78 to 0 °C; (2) Et3N, 0 °C to rt; (b) 25% HBr in acetic acid, rt or H2, Pd–C, MeOH, rt; and (c) DCC, HOSu, Et3N, DMF, 0 °C to rt.