4-Aminopyridine → (S)-4-(tert-butoxycarbonylamino)-N-(4-pyridyl)thiochromane-7-carboxamide

Participants

Reaction Steps

To an acetonitrile (75 ml) solution of (S)-4-(tert-butoxycarbonylamino)thiochromane-7-carboxylic acid (1.00 g) and 4-aminopyridine (335 mg) were added triethylamine (1.35 ml) and 2-chloro-1-methylpyridinium iodide (991 mg), and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture and extracted with ethyl acetate. The obtained organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate. The solvent of this solution was evaporated and purified by silica gel column chromatography (chloroform-methanol) to give the objective (S)-4-(tert-butoxycarbonylamino)-N-(4-pyridyl)thiochromane-7-carboxamide (845 mg) as pale yellow crystals.

Provenance & Evidence