Trifluoroacetic acid → 2,6-Diamino-N-(6-hydroxy-benzofuran-2-ylmethyl)-nicotinamide

Participants

Reaction Steps

To a trifluoroacetic acid (5 mL) solution of 2,6-diamino-N-(6-benzyloxy-benzofuran-2-ylmethyl)-nicotinamide (238 mg, 612 μmol) described in Example 1 was added thioanisole (287 μL, 2.45 mmol) at 0° C., which was stirred at room temperature for 2 hours. To the reaction solution were added sodium bicarbonate and water at 0° C., followed by extraction with ethyl acetate. After washing the organic layer with sat. NaCl, the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under a reduced pressure and the residue was purified by NH silica gel column chromatography (ethyl acetate:methanol=10:1) to obtain the title compound (101 mg, 55%) as a pale brown solid.

Provenance & Evidence