Sodium Hydroxide → HCID 21084001, compound

Participants

Reaction Steps

To a solution of the compound of Example 91 (134 mg, 0.27 mmol) in EtOH (0.5 mL) and water (0.73 mL) was added sodium hydroxide (0.27 mL of a 1M solution, 0.27 mmol) and the mixture heated at reflux for 5 h. The reaction was freeze dried to give 7-{4-[2-(2-Methyl-1H-imidazol-1-yl)ethoxy]phenyl}-6-oxo-3-phenyl-6,7-dihydrothieno[2,3-b]pyridine-2-carboxylic acid as a solid. LCMS (ES+) RT 2.34 minutes, 472 (M+H)+. This compound was dissolved in DMF (2 mL) and thionyl chloride (30 μL, 0.405 mmol) was added and the reaction stirred at r.t. for 5 mins. Aqueous ammonia (2 mL of a 25% solution) was added and the reaction stirred for 30 mins. The reaction was diluted with water (20 mL) and extracted with EtOAc (3×30 mL). The combined EtOAc extracts were washed with water (2×10 mL), brine (20 mL), dried (MgSO4) and concentrated in vacuo to give the title compound as a solid (104 mg, 82%). δH (CDCl3) 7.52–7.48 (3H, m), 7.37–7.33 (2H, m), 7.29–7.26 (2H, m), 7.20–7.18 (1H, m), 7.01–6.96 (3H, m), 6.90–6.88 (2H, m), 6.50 (1H, d, J 9.6 Hz), 4.23–4.20 (4H, m), 2.42 (3H, s). LCMS (ES+) RT 2.28 minutes, 471 (M+H)+.

Provenance & Evidence