Gemini c18 150x4.6mm column

¹H and NMR spectral data were recorded in CDCl₃ or DMSO-d₆ on a 300 or 400 MHz Bruker NMR spectrometer. Column chromatography was conducted on Revelaris flash chromatography system. Reactions were monitored using thin-layer chromatography (TLC) on silica gel plates. HPLC analysis was conducted on an Agilent 1100 series LC system (Agilent ChemStation Rev.A.10.02; Phenomenex-Luna-C18, 4.8 mm × 150 mm, 5 μm, 1.0 mL/min, UV 254nm, room temperature) with MeCN/H₂O (0.05% TFA or HCOOH buffer) gradient elution. HPLC-MS was performed on a Gilson 321 HPLC with detection performed by a Gilson 170 DAD and a Finnigan AQA mass spectrometer operating in electrospray ionization mode using a Phenomenex Gemini C18 150x4.6mm column. Compound purity was determined using an Agilent 1100 series LC system (Agilent ChemStation Rev.A.10.02; Phenomenex-Luna-C18, 4.8 mm × 150 mm, 5 μm, 1.0 mL/min, UV 254nm, room temperature) with MeCN/H₂O (0.05% TFA or HCOOH buffer) gradient elution. All compounds were >95% pure via LC/MS analysis.

The synthesis of the thiosemicarbazone 5 was according to procedures described previously [37 (link)]. Briefly, 1 eq of the acid and 1 eq of the hydrazine were dissolved in anhydrous ethanol and the resulting reaction mixture was refluxed overnight. The acetone was evaporated and the crude reaction mixture purified by column chromatography. ¹H and NMR spectral data were recorded in CDCl₃ or Acetone-d6 on a 300 MHz Bruker NMR spectrometer. Column chromatography was carried out on Revelaris flash chromatography system. Reactions were monitored using thin-layer chromatography (TLC) on silica gel plates. HPLC analysis was conducted on an Agilent 1100 series LC system (Agilent ChemStation Rev.A.10.02; Phenomenex-Luna-C18, 4.8 mm × 150 mm, 5 μm, 1.0 mL/min, UV 254nm, room temperature) with MeCN/H₂O (0.05% TFA or HCOOH buffer) gradient elution. HPLC-MS was performed on a Gilson 321 HPLC with detection performed by a Gilson 170 DAD and a Finnigan AQA mass spectrometer operating in electrospray ionization mode using a Phenomenex Gemini C18 150x4.6mm column. Yield: (0.011 g, 11%). ¹H NMR (300 MHz, MeOD): 2.55 (3H,CH3); 7.62–8.51 (6H, m). LCMS–ESI (M+H)⁺: 245.1.

¹H and ¹³C NMR spectral data were recorded in CDCl₃ or DMSO-d₆ on a 300 or 400 MHz Bruker NMR spectrometer. Column chromatography was conducted on silica gel (100–300 mesh). Reactions were monitored using thin-layer chromatography (TLC) on silica gel plates. HPLC analysis was conducted on an Agilent 1100 series LC system (Agilent ChemStation Rev.A.10.02; Phenomenex-Luna-C18, 4.8 mm × 150 mm, 5 μm, 1.0 mL/min, UV 254 nm, room temperature) with MeCN/H₂O (0.05% TFA or HCOOH buffer) gradient elution. HPLCMSwas performed on a Gilson 321 HPLC with detection performed by a Gilson 170 DAD and a Finnigan AQA mass spectrometer operating in electrospray ionisation mode using a Phenomenex Gemini C18 150x4.6 mm column. Purity was determined using a Waters Acquity UPLC system equipped with a BEH C18 1.7 μm 2.1 × 100 mm column.