Lithium Hydroxide → 6'-{[(Ethylamino)carbonyl]amino}-5''-fluoro-3,3':4',3''-terpyridine-5-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

Ethyl 6′-{[(ethylamino)carbonyl]amino}-5″-fluoro-3,3′:4′,3″-terpyridine-5-carboxylate (Example 68, 0.19 g, 0.46 mmol) was added to a 25 mL round-bottomed flask with THF (3 mL) to give a white suspension. Lithium hydroxide (1.160 mL, 1.16 mmol) was added to the mixture, and the solution was stirred at 45° C. for 2 h. The solvent was removed under reduced pressure, and the resulting residue was diluted with water and adjusted to pH˜4 by 2N HCl. The precipitate that formed was collected by filtration, washed with water, and dried to give the title compound as a white solid (154 mg). MS (ESP): 382 (MH+) for C19H16FN5O3; NMR: 1.08 (t, 3H), 3.13-3.24 (m, 2H), 7.63 (s, 1H) 7.64-7.68 (m, 1H) 7.69-7.77 (m, 1H), 7.93 (t, 1H), 8.19 (t, 1H), 8.36 (s, 1H), 8.45 (d, 1H), 8.55 (d, 1H), 8.90 (d, 1H), 9.45 (s, 1H).

Provenance & Evidence