1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 25235904, compound

Participants

Reaction Conditions

Reaction Steps

Add di-imidazol-1-yl-methanethione (72 mg, 0.403 mmol) to a solution of bicyclo[2.2.1]hept-2-ylamine (48 uL, 0.403 mmol) in DMF (1 mL) and stir for 3 hr. Add 2-(2,6-dichloro-phenyl)-3H-benzoimidazole-5-carboxylic acid hydrazide (100 mg, 0.310 mmol) and DMF (1 mL) to the reaction. Heat the mixture to 80° C. for 1.5 hr. Add EDCI (119 mg, 0.620 mmol) and heat for 1 hr. Allow the reaction to cool to room temp and dilute with water (15 mL). Collect the resulting precipitate by filtration. Suspend the solid in boiling ACN. Allow the suspension to cool to room temp and then 4° C. Filter to collect the white solid. Suspend the solid in 1 N NaOH (3 mL) and stir for 20 min. Filter and wash the solid with 1 N NaOH, water, and Et2O. Dry the solid in a vac oven to afford the title compound as a white solid: 1H NMR (400 MHz, MeOD) δ ppm 1.17-1.35 (m, 3H) 1.42-1.49 (m, 1H) 1.50-1.64 (m, 3H) 1.87 (ddd, J=12.98, 8.05, 2.08 Hz, 1H) 2.33 (br. s., 1H) 2.40 (d, J=4.04 Hz, 1H) 3.54 (dd, J=7.77, 2.84 Hz, 1H) 7.55-7.63 (m, 3H) 7.77 (d, J=8.34 Hz, 1H) 7.92 (dd, J=8.53, 1.20 Hz, 1H) 8.17 (s, 1H); MS (m/z) 439.9 (M+1).

Provenance & Evidence