Methanol → HCID 58094796, compound

Participants

Reaction Steps

To a solution of 2-(2-aminopyridin-4-yl)-4-(2,4-dichlorophenyl)-5-(1H-imidazol-5-yl)thiophene-3-carbonitrile (16.3 mg, 0.0395 mmol) in Pyridine (130.5 mg, 1.650 mmol) and DCM (1.0 mL, 16 mmol) was added acetic anhydride (108.2 mg, 1.060 mmol). The mixture was stirred at rt overnight. The solvent was evaporated and the residue was dissolved in MeOH (4 mL, 90 mmol). Sodium bicarbonate (0.5 g, 6 mmol) was added and followed by water. The mixture was stirred for 30 min. The mixture was concentrated and the residue was dissolved in EtOAc. The organic phase was washed with water and the organic layer was separated and dried over sodium sulfate. The crude product was obtained by evaporation and the purified by column chromatography to afford pure title compound as a yellow solid (12.4 mg, 69.4%). LC/MS (AA) ES+ 454, 456; ES− 452, 454. 1H-NMR (DMSO-d6, 300 MHz) δ: 12.63-12.07 (1H, br), 10.79-10.74 (1H, s), 8.57 (1H, s), 8.48 (1H, d, J=5.2 Hz), 7.94 (1H, d, J=1.89 Hz), 7.74 (1H, d, J=0.92 Hz), 7.62 (1H, s), 7.64 (1H, d, J=1.98 Hz), 7.51 (1H, dd, J=5.3, 1.7 Hz), 6.30 (1H, d, J=0.94 Hz), 2.13 (3H, s)

Provenance & Evidence