Water → HCID 68183339, compound

Participants

Reaction Steps

To a mixture of rel-(4R,5R)-4-(3,4-dichlorophenyl)-2-(morpholin-4-yl)-7-oxo-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-5-carboxylic acid (0.100 g, 0.234 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.090 g, 0.47 mmol), 1-hydroxybenzotriazole hydrate (0.072 g, 0.47 mmol) in methylene chloride (4 mL) was added a solution of 33% ammonium hydroxide in water (0.40 mL, 4.7 mmol). The mixture was stirred at rt overnight. The mixture was concentrated and the residue was purified by silica gel chromatography. Final purification by HPLC afforded the product as a white solid. LCMS: (AA), ES+: 426, 428, 1H NMR (400 MHz, DMSO) δ 7.58 (d, J=8.3 Hz, 1H), 7.53-7.47 (m, 2H), 7.37 (d, J=4.2 Hz, 1H), 7.20 (s, 1H), 7.10 (dd, J=8.5, 2.0 Hz, 1H), 6.00 (s, 1H), 4.52 (s, 1H), 3.96 (dd, J=4.3, 2.2 Hz, 1H), 3.73-3.63 (m, 4H), 3.12 (d, J=5.6 Hz, 4H).

Provenance & Evidence