Ammonium Hydroxide → HCID 68183031, compound

Participants

Reaction Steps

To a solution of 2-(4-(4-chlorophenyl)-2-morpholino-7-oxo-4,5-dihydrothieno[2,3-c]pyridin-6(7H)-yl)acetic acid (95.2 mg, 0.234 mmol) in DMF (3.0 mL) was added 1-hydroxybenzotriazole hydrate (39.4 mg, 0.297 mmol) and N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (80.7 mg, 0.421 mmol) and the resulting solution was stirred for 30 minutes. 33% NH4OH (202 uL, 2.34 mmol) was added and the resulting solution was stirred at room temperature overnight. The reaction was diluted with ethyl acetate (40 mL) and water (15 mL). The layers were separated and the organic layer was washed with water (3×10 mL). The organic layer was dried over MgSO4, filtered and concentrated in vacuo to give 77 mg crude. The residue was purified by analytical chromatography to give 50 mg (53% yield) of the title compound as a white solid. LC/MS (FA) ES+ 406. 1H NMR (400 MHz, DMSO-d6) δ: 7.42-7.39 (m, 2H), 7.28-7.26 (m and bs, 3H total), 7.01 (bs, 1H), 5.78 (s, 1H), 4.30-4.27 (m, 1H), 4.04 (d, 1H, J=17.2 Hz), 3.84-3.79 (m, 1H), 3.77 (d, 1H, J=17.2 Hz), 3.70-3.67 (m, 4H), 3.64-3.59 (m, 1H), 3.13-3.10 (m, 4H).

Provenance & Evidence