Trimethyl Phosphate → 5-(4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2-oxo-2H-chromen-8-yloxy)pentyl dihydrogen phosphate

Participants

Reaction Steps

Phosphoryl trichloride (69.4 mg, 0.46 mmol) was added to a solution of 4-(3,5-dichloropyridin-4-ylamino)-8-(5-hydroxypentyloxy)-7-methoxy-2H-chromen-2-one (100 mg, 0.22 mmol, Example 72) and trimethyl phosphate (2 mL). After 1 h at rt, water (0.5 mL) was added, and the reaction was stirred for an additional 2 h. The solution was directly purified by reverse-phase HPLC to give 5-(4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2-oxo-2H-chromen-8-yloxy)pentyl dihydrogen phosphate: 1H NMR (400 MHz, DMSO-d6): δ 10.88 (br, 2H), 9.52 (s, 1H), 8.81 (s, 2H), 7.94 (d, 1H), 7.20 (d, 1H), 4.64 (s, 1H), 3.98 (t, 2H), 3.92 (s, 3H), 3.82 (m, 2H), 1.70 (m, 2H), 1.62 (m, 2H), 1.51 (m, 2H); MS (ESI): 518.9.

Provenance & Evidence