Methanol → 5-chloro-4-(8-(cyclopentyloxy)-7-methoxy-2-oxo-2H-chromen-4-ylamino)nicotinic acid

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Reaction Steps

Lithium hydroxide (1 mL, 1M, 1 mmol) was added to a solution of methyl 5-chloro-4-(8-(cyclopentyloxy)-7-methoxy-2-oxo-2H-chromen-4-ylamino)nicotinate, MeOH (0.8 mL), and THF (1.2 mL). The mixture was stirred for 3 h, quenched with 1N HCl (3 mL), and extracted with EtOAc. The organic extract was dried, filtered, concentrated and purified by reverse-phase HPLC (25→100% MeCN/H2O) to give 5-chloro-4-(8-(cyclopentyloxy)-7-methoxy-2-oxo-2H-chromen-4-ylamino)nicotinic acid: 1H NMR (400 MHz, DMSO-d6): δ 9.53 (s, 1H), 8.97 (s, 1H), 8.92 (s, 1H), 7.85 (d, 1H), 7.19 (d, 1H), 4.83 (m, 1H), 4.74 (s, 1H), 3.90 (s, 3H) 1.85-1.54 (m, 8H); MS (ESI): 430.9.

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