Diisopropylethylamine → N-(4-amino-2-oxo-1,2-dihydropyridin-3-yl)-2-(phenylamino)quinoline-8-carboxamide

Participants

Reaction Steps

A mixture of 2-(phenylamino)quinoline-8-carboxylic acid (0.42 g, 1.589 mmol), 3,4-diaminopyridin-2(1H)-one (0.199 g, 1.589 mmol, Sphinx Scientific Laboratory LLC, Sycamore, Ill.), 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate (V) (0.604 g, 1.589 mmol), and N-ethyl-N-isopropylpropan-2-amine (0.277 ml, 1.589 mmol) in DMF (1.589 ml) was stirred at RT for 2 h. The reaction was diluted with (3:2) CHCl3/IPA (200 ml), added to a separatory funnel, and washed with water (2×50 ml) before the organic layer was separated, dried over Na2SO4, and concentrated to give N-(3-amino-2-oxo-1,2-dihydropyridin-4-yl)-2-(phenylamino)quinoline-8-carboxamide (or N-(4-amino-2-oxo-1,2-dihydropyridin-3-yl)-2-(phenylamino)quinoline-8-carboxamide; regiochemistry not established) as a brown amorphous solid. MS (ESI, pos. ion) m/z: 372.2 (M+1).

Provenance & Evidence