Diisopropylethylamine → 7-Methoxy-2-oxo-2H-chromene-3-carboxylic acid (3-imidazo[1,2-a]pyridin-2-yl-phenyl)-amide

Participants

Reaction Steps

DIEA (0.027 mL, 0.16 mmol) was added to 7-methoxy-3-carboxy-coumarin (0.031 g, 0.14 mmol) and HATU (0.060 g, 0.16 mmol) in 2 mL of dimethylformamide (DMF) with constant stirring at room temperature until a clear solution resulted. Subsequently, 3-Imidazo[1,2-a]pyridin-2-yl-phenylamine (0.030 g, 0.14 mmol) was added and allowed to react for approximately 30 minutes, when a yellow solid precipitated out of solution. The precipitate was filtered and dried under suction and then in vacuo to give 0.051 g of 1541C in an 86% yield: 1H NMR (400 MHz, CD3OD/CDCl3) δ 10.95 (s, 1H), 8.96 (s, 1H), 8.23 (dd, J=1.8, 1.9 Hz, 1H), 8.20 (d, J=7.1 Hz, 1H), 7.99 (s, 1H), 7.79 (d, J=7.7 Hz, 1H), 7.75 (d, J=8.1 Hz, 1H), 7.68 (d, J=8.6 Hz, 1H), 7.63 (d, J=9.1 Hz, 1H), 7.48 (dd, J=7.9, 8.0 Hz, 1H), 7.25 (dd, J=5.5, 6.8 Hz, 1H), 7.01 (dd, J=2.4, 8.8 Hz, 1H), 6.95 (d, J=2.4 Hz, 1H), 6.85 (dd, J=7.0, 7.3 Hz, 1H), 3.96 (s, 3H); LCMS (ESI) m/z 412 (MH+).

Provenance & Evidence