Hydrochloric Acid → HCID 66743236, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 5-bromo-3-[(pyridin-4-ylmethyl)amino]thiophene-2-carboxylate (238 mg, 0.727 mmol) in MeOH (2 mL) and ethanol (10 mL) was added a solution of sodium hydroxide (87 mg, 2.18 mmol) in water (1 mL). After stirring at 100° C. for 5 h, 6 M aqueous HCl (0.23 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 (4 mL). Then, triethylamine (2.0 mL, 15 mmol) and ammonium chloride (777 mg, 15 mmol) were added. After stirring at room temperature for 5 min, 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (836 mg, 4.4 mmol) and 1-hydroxybenzotriazole (589 mg, 4.4 mmol) were added to the mixture, and 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 (167 mg, 74%) as a brown solid:

Provenance & Evidence