Ethanol → 6-(6-(3-Ethylureido)pyridin-3-yl)-1-(2-methoxyethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

A suspension of ethyl 6-(6-(3-ethylureido)pyridin-3-yl)-1-(2-methoxyethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate (Example 42, 59 mg, 0.13 mmol) and sodium hydroxide (0.202 mL, 0.40 mmol) in tetrahydrofuran (1 mL) was heated to 60° C. After 2 h, the reaction was not yet complete. Ethanol (2 mL) was added and the reaction was heated for another 1 h, then cooled to room temperature and concentrated under reduced pressure. The resulting solid was dissolved in water and acidified to pH 4 with 10% HCl. The solid that formed was collected by filtration and placed under high vacuum to remove residual water. MS (ESP): 411 (M+H+) for C21H22N4O5; NMR: 1.11 (t, J=6 Hz, 3H), 3.20 (m, 2H), 3.23 (s, 3H), 3.74 (m, 2H), 4.83 (m, 2H), 7.50 (m, 1H), 8.01 (br s, 1H), 8.21 (m, 1H), 8.31 (m, 1H), 8.58 (m, 1H), 8.69 (m, 1H), 8.94 (s, 1H), 9.38 (s, 1H), 15.20 (s, 1H).

Provenance & Evidence