Hydrochloric Acid → HCID 66743363, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3 M sodium hydroxide (2.5 mL, 7.50 mmol), MeOH (10 mL) and methyl 5-bromo-3-(methylamino)thiophene-2-carboxylate (674 mg, 2.69 mmol) was stirred at 70° C. overnight. Then, the mixture was cooled in ice-water bath, and 6 M HCl (0.9 mL, 5.40 mmol) was added. The mixture was concentrated under reduced pressure to give a yellow solid. This residue was mixed with ammonium chloride (2.88 g, 53.9 mmol), triethylamine (7.51 mL, 53.9 mmol) and DMF (27 mL). The mixture was stirred for 5 min, then 1-hydroxybenzotriazole (2.19 g, 16.2 mmol) and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (3.10 g, 16.2 mmol) were added. The stirring was continued for 3 days. The reaction mixture was poured into saturated aqueous NaHCO3 (200 mL). Extraction with EtOAc (200 mL), washing with saturated NaHCO3, drying over MgSO4, filtration and concentration under reduced pressure gave brown oil. This oil was purified by column chromatography (Purif, silica gel, hexane to EtOAc) to afford the title compound (536 mg, 85%) as a pale brown solid:

Provenance & Evidence