3-Aminopyridine → {5-[2-(2,6-Dichloro-phenyl)-3H-benzoimidazol-5-yl]-[1,3,4]oxadiazol-2-yl}-pyridin-3-yl-amine

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Reaction Steps

Combine 3-aminopryidine (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 (25-65% ACN/H2O+5 mM NH4OH) to afford the title compound: 1H NMR (400 MHz, DMSO-d6) δ ppm 7.44 (dd, J=8.34, 4.80 Hz, 1H) 7.63-7.67 (m, 1H) 7.70 (s, 1H) 7.72 (d, J=1.77 Hz, 1H) 7.87 (br. s., 2H) 8.13 (ddd, J=8.40, 2.59, 1.39 Hz, 2H) 8.25 (dd, J=4.80, 1.26 Hz, 1H) 8.80 (d, J=2.53 Hz, 1H) 10.98 (s, 1H) 13.30 (br. s., 1H); MS (m/z) 423.1 (M+1).

Provenance & Evidence