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. 2020 Mar 19;11(5):977–983. doi: 10.1021/acsmedchemlett.0c00014

Scheme 1. Synthesis of Hybrid Compounds 4 and 5.

Scheme 1

Reagents and conditions: a) triethylamine, dry ethanol, 80 °C; b) Zn(0), NH4Cl, H2O:1,4-dioxane 1:1, 50 °C; c) 1) trichloroacetyl chloride, dry dichloroethane, 70 °C; 2) 2 N KOH aqueous solution, ethanol/tetrahydrofuran 1:1; d) N,N-dimethylformamide di-tert-butyl acetal, dry toluene, 90 °C; e) triethylamine, dry dichloromethane, RT; f) trifluoroacetic acid, dry dichloromethane, RT; g) triethylamine, TBTU reagent, dry N,N-dimethylformamide, RT; h) LiOH(aq), tetrahydrofuran, RT; (i) 1) triethylamine, TBTU reagent, O-(tetrahydro-2H-pyran-2-yl)hydroxylamine, dry N,N-dimethylformamide, RT; 2) 4 N hydrogen chloride solution in 1,4-dioxane, dry tetrahydrofuran, RT.