Water → 4-(3,5-dichloropyridin-4-ylamino)-8-(((2S,3R,4S)-3,4-dihydroxy-5-oxotetrahydrofuran-2-yl)methoxy)-7-methoxy-2H-chromen-2-one

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Reaction Steps

Trifluoroacetic acid (0.1 mL) was added to a mixture of 4-(3,5-dichloropyridin-4-ylamino)-8-(((3aS,4S,6aS)-2,2-dimethyl-6-oxotetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methoxy)-7-methoxy-2H-chromen-2-one (60 mg, 0.12 mmol, Example 50), water (0.1 mL), and THF (3 mL). The mixture was stirred at rt for 2 d. Then, more trifluoroacetic acid (3 mL) was added over time until the reaction was complete by LCMS. The mixture was concentrated to give 4-(3,5-dichloropyridin-4-ylamino)-8-(((2S,3R,4S)-3,4-dihydroxy-5-oxotetrahydrofuran-2-yl)methoxy)-7-methoxy-2H-chromen-2-one: 1H NMR (400 MHz, DMSO-d6): δ 9.55 (s, 1H), 8.81 (s, 2H), 7.97 (d, 1H), 7.21 (d, 1H), 5.74 (s, 1H), 4.63 (s, 1H), 4.61 (d, 1H), 4.49 (m, 1H), 4.42 (d, 1H), 4.23 (d, 1H), 3.91 (s, 3H); MS (ESI): 482.8.

Provenance & Evidence