Hydrochloric Acid → HCID 66743310, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 5-bromo-3-[(pyridin-3-ylmethyl)amino]thiophene-2-carboxylate (260 mg, 0.795 mmol) in MeOH (3 mL) was added a solution of sodium hydroxide (96 mg, 2.39 mmol) in water (1.5 mL). After stirring at 80° C. for 5 h, 6 M aqueous HCl (0.25 mL) was added to the mixture to adjust the pH to 10. After removal of the solvent at reduced pressure, the residue was suspended with DMF (5 mL). Then, triethylamine (2.2 mL, 16 mmol) and ammonium chloride (850 mg, 16 mmol) were added. After stirring at room temperature for 5 min, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (914 mg, 4.8 mmol) and 1-hydroxybenzotriazole (645 mg, 4.8 mmol) were added to the mixture, and the stirring was continued for 18 h. Then, water and EtOAc were 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, 90:10 hexane/EtOAc to EtOAc) to give the title compound (175 mg, 71%) as a yellow solid:

Provenance & Evidence