Hydrochloric Acid → HCID 66743408, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 5-bromo-3-[(pyridin-2-ylmethyl)amino]thiophene-2-carboxylate (336 mg, 1.03 mmol) in MeOH (3 mL) and ethanol (10 mL) was added a solution of sodium hydroxide (124 mg, 3.09 mmol) in water (1.5 mL). After stirring at 100° C. for 5 h, 6 M aqueous HCl (0.33 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 (5 mL). Then, triethylamine (2.9 mL, 21 mmol) and ammonium chloride (1.1 g, 21 mmol) were added. After stirring at room temperature for 5 min, 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (1.2 g, 6.2 mmol) and 1-hydroxybenzotriazole (835 mg, 6.2 mmol) were added to the mixture, and stirring was continued for 18 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, 95:5 hexane/EtOAc to EtOAc) to give the title compound (160 mg, 50%) as a yellow solid:

Provenance & Evidence