Hydrochloric Acid → HCID 54689826, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of NaH (60% suspension in mineral oil, pre washed with hexanes, 0.430 g, 10.73 mmol) in THF (25 mL) was added a solution of 4-(4-chlorophenyl)-2-(2-ethoxycarbonyl acetylamino)-thiophene-3-carboxylic acid ethyl ester (1.9308 g, 4.88 mmol) in THF (25 mL) dropwise via syringe. The reaction mixture was then heated to reflux for 3 hrs, cooled to 0° C. and quenched by dropwise addition of MeOH (5 mL) and H2O (2 mL). The reaction mixture was concentrated to give a crude solid which was then dissolved in MeOH (30 mL) and 40% NaOH (30 mL). The resulting mixture was heated at for 5 hours, cooled to room temperature and acidified with concentrated HCl. The mixture was concentrated under reduced pressure and DMSO/MeOH (1:1) was used to dissolve the residue and filtered. The filtrate was purified on a RP-HPLC system to afford the title compound. MS (ESI) m/e 275.9 (M−H)+; 1H NMR (400 MHz, DMSO-d6): δ ppm 11.55 (br s, 1H), 10.92 (s, 1H), 7.47–7.39 (m, 4H), 7.06 (s, 1H), 5.74 (s, 3H).

Provenance & Evidence