1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 25235948, compound

Participants

Reaction Conditions

Reaction Steps

Combine 3-amino-6-methyl-pyridine (66 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. Filter the combined aqueous layers and wash the collected solid with Et2O. Suspend the solid in boiling toluene/EtOAc. Allow the suspension to cool to 4° C. and collect the solid. Wash with Et2O. Purify the solid by reverse phase HPLC (20-65% ACN/H2O+5 mM NH4OH) to afford the title compound: 1H NMR (400 MHz, DMSO-d6) δ ppm 2.46 (s, 3H) 7.33 (d, J=8.34 Hz, 1H) 7.64-7.68 (m, 1H) 7.71 (s, 1H) 7.73 (d, J=2.02 Hz, 1H) 7.86 (br. s., 2H) 8.04 (dd, J=8.40, 2.46 Hz, 1H) 8.13 (br. s., 1H) 8.70 (d, J=2.53 Hz, 1H) 10.88 (br. s., 1H); MS m/z=437.0 (M+1).

Provenance & Evidence