N,N-Dimethylaniline → 8-(cyclopentyloxy)-4-(3,5-dichloropyridin-4-ylamino)-3-(2-hydroxyethyl)-7-methoxy-2H-chromen-2-one

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Reaction Steps

N,N-Dimethylaniline (174 mg, 1.44 mmol) and aluminum trichloride (143 mg, 1.08 mmol) were sequentially added to a solution of 3-(2-(benzyloxy)ethyl)-8-(cyclopentyloxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2H-chromen-2-one (100 mg, 0.18 mmol) and dichloromethane (10 mL). The reaction was refluxed for 8 h, allowed to cool to rt, quenched with cold water (1 mL), and then poured into ice water (20 mL). The mixture was extracted with dichloromethane (15 mL×3), and the combined extracts were dried, filtered, concentrated, and purified by silica gel chromatography (ethyl acetate:petroleum ether) to give 8-(cyclopentyloxy)-4-(3,5-dichloropyridin-4-ylamino)-3-(2-hydroxyethyl)-7-methoxy-2H-chromen-2-one: 1H NMR (400 MHz, DMSO-d6): δ 9.26 (s, 1H), 8.47 (s, 2H), 6.94 (d, 1H), 6.85 (d, 1H), 5.58 (m, 1H), 4.83 (m, 1H), 3.81 (s, 3H), 3.60 (m, 2H), 2.68 (m, 2H), 1.90-1.50 (m, 8H); MS (ESI): 464.9.

Provenance & Evidence