1,2-Dichloroethane → HCID 67136005, compound

Participants

Reaction Steps

To a solution of N′-hydroxy-2-(hydroxymethyl)isonicotinimidamide (Example 66, Step 1; 0.100 g; 0.30 mmol) and Intermediate A1 (0.108 g; 0.42 mmol) in MeCN (3 mL) was added EDC (0.060 g; 0.38 mmol). The reaction mixture was stirred at ambient temperature for 18 h. The reaction mixture was diluted with pyridine (2 mL) and heated at 150° C. in the microwave for 30 minutes. This process was repeated 4 times and combined for work-up. 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 compound. 1H NMR (CDCl3, 400 MHz) δ 8.76 (1 H, d, J=5.2 Hz), 8.44 (1 H, s), 8.18 (1 H, dd, J=7.9, 1.9 Hz), 8.06 (1 H, s), 7.99 (1 H, d, J=5.2 Hz), 7.39-7.22 (4 H, m), 7.13 (1 H, d, J=7.5 Hz), 4.90 (2 H, s), 4.28-4.18 (2 H, m), 3.65 (1 H, br s), 3.34 (3 H, s), 2.08 (3 H, s). LC/MS: 388 (M+H)+. HPLC (Method B) Rt 3.91 min (Purity: 98.1%).

Provenance & Evidence