4-Aminopyridine → HCID 25235900, compound

Participants

Reaction Steps

Combine 4-amino pyridine (30 mg, 0.312 mmol) and di-imidazol-1-yl-methanethione (56 mg, 0.312 mmol) in DMF (0.3 mL) and stir for 2 days. Add 2-(2,6-dichloro-phenyl)-3H-benzoimidazole-5-carboxylic acid hydrazide (77 mg, 0.240 mmol) and dilute with DMF (1.5 mL). Heat the reaction to 80° C. for 1 hr. Add EDCI (92 mg, 0.480 mmol) and heat for 1 hr at 80° C. Allow reaction to cool to room temp and dilute the reaction with water. Collect the resulting precipitate by filtration. Purify the solid by reverse-phase HPLC (20-50% ACN/H2O+5 mM NH4OH) to afford the title compound: 1H NMR (400 MHz, DMSO-d6) δ ppm 7.63-7.68 (m, 1H) 7.71 (s, 1H) 7.73 (d, J=2.02 Hz, 1H) 7.76-7.97 (m, 4H) 8.05-8.27 (m, 1H) 8.58 (d, J=6.44 Hz, 2H) 13.34 (br. s., 1H); MS (m/z) 423.0 (M+1).

Provenance & Evidence