Sodium Hydroxide → HCID 11603236, compound

Participants

Reaction Steps

A solution of Example 37F (0.68 g, 1.56 mmol) in a mixture of 5 ml tetrahydrofuran and 5 ml methanol was treated with sodium hydroxide (5M in methanol, 3 ml, 15 mmol), and the reaction stirred at ambient temperature for 2 hours. The reaction mixture was diluted with water, and the precipitate that formed was collected by filtration. After drying, the solid was purified using reverse-phase HPLC (acetonitrile-water with 0.1% trifluoroacetic acid as eluent) to provide 0.29 g of title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 13.01 (s, 1 H), 8.59 (s, 1 H), 8.03 (s, 1 H), 7.67 (d, J=7.46 Hz, 1 H), 7.62 (d, J=7.80 Hz, 1 H), 7.55 (d, J=7.80 Hz, 1 H), 7.22 (t, J=7.80 Hz, 1 H), 7.04-7.11 (m, 2 H), 6.96 (d, J=7.80 Hz, 1 H), 4.96-5.03 (m, 1 H), 4.41-4.49 (m, 1 H), 4.30 (m, 1 H), 2.18 (m, 1 H), 2.06-2.13 (m, 1 H). MS (ESI) m/e 377 (M+H)+. Calcd. For C18H15N4O2F3.0.15 trifluoroacetic acid: C, 55.87; H, 3.88; N, 14.24. Found C, 55.95; H, 3.82; N, 14.28.

Provenance & Evidence