1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 25235255, compound

Participants

Reaction Steps

Combine 3-amino-6-chloro-pyridine (78 mg, 0.606 mmol) and di-imidazol-1-yl-methanethione (108 mg, 0.606 mmol) in DMF (1.5 mL) and stir for 4 hr. Add 2-(2,6-dichloro-phenyl)-3H-benzoimidazole-5-carboxylic acid hydrazide (150 mg, 0.466 mmol) and DMF (1 mL). Stir for 3 days. Add EDCI (179 mg, 0.932 mmol) and heat to 80° C. for 45 min. Upon cooling, dilute the reaction with EtOAc (50 mL) and extract with water (10 mL) and 1 N NaOH (10 mL). Combine the aqueous layers and allow to stand overnight. Evaporate the organic phase. Filter the combined aqueous layers and wash the collected solid with Et2O. Combine the solid with the residue from the organic phase and purify the material by reverse phase HPLC (20-65% ACN/H2O+5 mM NH4OH) to afford the title compound: 1H NMR (400 MHz, DMSO-d6) δ ppm 7.56 (d, J=8.72 Hz, 1H) 7.63-7.68 (m, 1H) 7.70 (s, 1H) 7.72 (d, J=2.02 Hz, 1H) 7.86 (br. s., 2H) 8.13 (br. s., 1H) 8.16 (dd, J=8.78, 2.97 Hz, 1H) 8.64 (d, J=2.91 Hz, 1H) 11.16 (s, 1H) 13.31 (br. s., 1H); MS m/z=458.9 (M+1).

Provenance & Evidence