Triethylamine → Methyl 6-[(3-{[(benzyloxy)carbonyl](methyl)amino}propyl)(methyl)carbamoyl]pyridine-3-carboxylate

Participants

Reaction Steps

5-(Methoxycarbonyl)pyridine-2-carboxylic acid (700 mg, 3.86 mmol) was dissolved in methylene chloride (40 mL), triethylamine (0.805 mL, 5.79 mmol) and pivaloyl chloride (0.524 mL, 4.25 mmol) were added under ice cooling, and the mixture was stirred at room temperature for 15 minutes. The reaction mixture was added dropwise to a solution of N,N′-dimethylpropanediamine (1.18 g, 11.6 mmol) in methylene chloride (40 mL) under ice cooling, and the mixture was stirred overnight at room temperature. Triethylamine (4.03 mL, 29.0 mmol) and benzyloxycarbonyl chloride (4.14 mL, 29.0 mmol) were added under ice cooling, and the mixture was stirred at room temperature for 2 hours. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:3→0:100, v/v) to give the title compound (1.23 g; yield, 80%) as a colorless oily substance.

Provenance & Evidence