1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 25235254, compound

Participants

Reaction Conditions

Reaction Steps

Combine 3-amino-6-methoxy-pyridine (64 uL, 0.606 mmol) and di-imidazol-1-yl-methanethione (108 mg, 0.606 mmol) in DMF (1.5 mL) and stir for 3 hr. Add 2-(2,6-dichloro-phenyl)-3H-benzoimidazole-5-carboxylic acid hydrazide (150 mg, 0.466 mmol) and DMF (1 mL). Heat to 80° C. for 1 hr. Add EDCI (179 mg, 0.932 mmol) and heat to 80° C. for 1 hr. Upon cooling, dilute the reaction with EtOAc (50 mL) and extract with water (10 mL). Dry the organic phase over Na2SO4 and concentrate. Triturate the concentrate with hot EtOAc/toluene to obtain a white solid. Suspend the solid in saturated NaHCO3 and stir vigorously. Collect the solid and purify by silica gel chromatography (10-100% EtOAc/HEP, 0-50% MeOH/DCM) to afford the title compound as a white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 3.84 (s, 3H) 6.89 (d, J=8.84 Hz, 1H) 7.62-7.67 (m, 1H) 7.70 (s, 1H) 7.72 (d, J=1.64 Hz, 1H) 7.76 (tautomer, d, J=8.46 Hz, 1H) 7.81 (tautomer, dd, J=8.46, 1.26 Hz, 1H) 7.85-7.92 (mixture of tautomers, m, 1H) 7.96-8.01 (m, 1H) 8.03 (tautomer, s, 1H) 8.16 (tautomer, s, 1H) 8.44 (s, 1H) 10.63 (s, 1H) 13.28 (s, 1H); MS m/z=453.0 (M+1).

Provenance & Evidence