Potassium Carbonate → 4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-8-(5-(4-methylpiperazin-1-yl)pentyloxy)-2H-chromen-2-one

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Reaction Steps

1-Methylpiperazine (0.2 mL, 1.8 mmol) was added to a solution of 8-(5-bromopentyloxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2H-chromen-2-one (50 mg, 0.1 mmol, Example 28) and DMSO (1.5 mL). After 10 h, the reaction was poured into 10% K2CO3 (30 mL) and extracted with ethyl acetate (30 mL×3). The combined organic extracts were dried, filtered, concentrated, and purified by reverse-phase HPLC (acetonitrile:water) to give 4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-8-(5-(4-methylpiperazin-1-yl)pentyloxy)-2H-chromen-2-one: 1H NMR (400 MHz, DMSO-d6): δ 9.45 (br s, 1H), 8.71 (s, 2H), 7.90 (d, 1H), 7.13 (d, 1H), 4.46 (br s, 1H), 3.97 (t, 2H), 3.90 (s, 3H), 2.60-2.20 (br, 10H), 2.21 (s, 3H), 1.68 (m, 2H), 1.47 (m, 4H); MS (ESI): 520.9.

Provenance & Evidence