1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 25235258, compound

Participants

Reaction Steps

Combine 3-amino-6-trifluoromethyl-pyridine (98 mg, 0.606 mmol) and di-imidazol-1-yl-methanethione (108 mg, 0.606 mmol) in DMF (1.5 mL) and stir overnight. Add 2-(2,6-dichloro-phenyl)-3H-benzoimidazole-5-carboxylic acid hydrazide (150 mg, 0.466 mmol) and DMF (1 mL). Stir for 6.5 hr. Add EDCI (179 mg, 0.932 mmol) and heat to 80° C. for 1 hr. Upon cooling, dilute the reaction with EtOAc (75 mL) and extract with water (15 mL). Dry the organic phase over Na2SO4 and evaporate the solvent. Purify the residue by silica gel chromatography (3-6% MeOH/DCM) to afford the title compound as an off white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 7.62-7.68 (m, 1H) 7.71 (d, J=1.01 Hz, 1H) 7.73 (t, J=1.77 Hz, 1H) 7.78 (tautomer, d, J=8.59 Hz, 1H) 7.82-7.87 (tautomer, m, 1H) 7.90-7.94 (m, 1H) 7.96 (d, J=8.72 Hz, 1H) 8.08 (tautomer, d, J=0.88 Hz, 1H) 8.21 (tautomer, s, 1H) 8.38 (d, J=8.59 Hz, 1H) 8.90 (d, J=2.27 Hz, 1H) 11.51 (s, 1H) 13.32 (d, J=2.91 Hz, 1H); MS m/z=490.9 (M+1).

Provenance & Evidence