Hydrochloric Acid → HCID 66743752, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 5-bromo-3-[(3-nitrobenzyl)amino]thiophene-2-carboxylate (495 mg, 1.33 mmol) in MeOH (4 mL) was added a solution of sodium hydroxide (160 mg, 3.99 mmol) in water (2 mL). After stirring at 60° C. for 4 h, 6 M aqueous HCl (0.42 mL) was added to the mixture to adjust the pH to 10. After removal of the solvent at reduced pressure, the residue was diluted with DMF (6 mL). Then, triethylamine (3.7 mL, 27 mmol) and ammonium chloride (1.4 g, 27 mmol) were added. After stirring at room temperature for 5 min, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.5 g, 8.0 mmol) and 1-hydroxybenzotriazole (1.1 g, 8.0 mmol) were added to the mixture, and stirring was continued for 17 h. Then, water was added to quench the reaction. The organic materials were extracted with EtOAc. The combined extracts were washed with water and brine, dried over Na2SO4 and filtered. After removal of the solvent at reduced pressure, the residue was purified by column chromatography (Purif, silica gel, hexane to 50:50 hexane/EtOAc) to give the title compound (269 mg, 57%) as a yellow solid:

Provenance & Evidence