1,2-Dichloroethane → HCID 178494467, compound

Participants

Reaction Steps

To a solution of 5-chloro-N′,6-dihydroxynicotinimidamide (Bionet, 1.46 g; 7.78 mmol) and Intermediate A1 (1.66 g; 6.48 mmol) in MeCN (50 mL) was added EDC (1.61 g; 8.42 mmol). The reaction mixture was stirred at ambient temperature for 18 h. The reaction mixture was diluted with pyridine (20 mL) and heated at 115° C. for 24 hours. The solvent was removed in vacuo and the residue dissolved in DCM. The mixture was washed with water and the organic phase passed through a hydrophobic frit. The solvent was evaporated in vacuo. The residue was purified by flash chromatography on silica, eluting with iso-hexane/EtOAc (100% iso-hexane to 100% EtOAc) to afford the title product as an off-white solid. 1H NMR (DMSO-d6, 400 MHz) δ 12.84 (1 H, s), 8.32 (1 H, s), 8.26 (1 H, d, J=2.3 Hz), 8.21 (1 H, d, J=2.4 Hz), 8.17 (1 H, dd, J=7.9, 1.9 Hz), 7.45 (1 H, d, J=7.9 Hz), 7.41-7.37 (2 H, m), 7.34-7.29 (1 H, m), 7.17 (1 H, d, J=7.4 Hz), 4.22 (2 H, q, J=9.4 Hz), 3.27 (3 H, s), 2.06 (3 H, s). LC/MS: 408 (M+H)+. HPLC (Method C) Rt 3.79 min (Purity: 99.4%).

Provenance & Evidence