Acetic Acid → N-(2,4-dimethoxybenzyl)-5-(1-(tetrahydro-2H-pyran-4-yl)pyrrolidin-2-yl)-N-(thiazol-2-yl)naphthalene-2-sulfonamide

Participants

Reaction Steps

N-(2,4-dimethoxybenzyl)-5-(pyrrolidin-2-yl)-N-(thiazol-2-yl)naphthalene-2-sulfonamide (Intermediate NN, 0.033 g, 0.065 mmol) and tetrahydro-4h-pyran-4-one (8.97 μl, 0.097 mmol) were dissolved in DCM (0.648 ml). Sodium triacetoxyborohydride (0.041 g, 0.194 mmol) and acetic acid (5.56 μl, 0.097 mmol) were added and the reaction was stirred for three hours at room temperature. 1M sodium hydroxide solution was added followed by ethyl acetate, and the reaction was stirred for one hour. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were dried with sodium sulfate, filtered, and concentrated to afford crude N-(2,4-dimethoxybenzyl)-5-(1-(tetrahydro-2H-pyran-4-yl)pyrrolidin-2-yl)-N-(thiazol-2-yl)naphthalene-2-sulfonamide as an off-white solid. m/z (ESI) 594.3 (M+H)+.

Provenance & Evidence