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. 2023 Mar 21;66(7):5208–5222. doi: 10.1021/acs.jmedchem.3c00151

Scheme 1. Synthesis of Amine-Substituted IT1t Derivatives.

Scheme 1

Reagents and conditions: (a) two steps: (1) 1,3-dichloroacetone, acetonitrile, reflux, 2 h.; (2) diglyme, 140 °C, 2 h, 67% over two steps; (b) dichloromethane, 20 h rt, 85–98%; (c) acetonitrile, 16 h, reflux, 40–48%; (d) TFA, dichloromethane, 3 h, rt, quant.; (e) BODIPY-SE, DIPEA, acetonitrile, rt, 3–4 h, 62%; and (f) 1-(6-((2,5-dioxopyrrolidin-1-yl)oxy)-6-oxohexyl)-3,3-dimethyl-2-((1E,3E)-5-((Z)-1,3,3-trimethyl-5-sulfoindolin-2-ylidene)penta-1,3-dien-1-yl)-3H-indol-1-ium-5-sulfonate (sulfo-cyanine5 NHS ester), DIPEA, DMF, 16 h, 81%.