Lithium Hydroxide → 4-[(Dimethylamino)carbonyl]-2-(6-{[(ethylamino)carbonyl]amino}pyridin-3-yl)-1,3-thiazole-5-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of ethyl 4-dimethylcarbamoyl-2-[6-(3-ethyl-ureido)-pyridin-3-yl]-thiazole-5-carboxylate (Example 52, 0.7 g, 1.78 mmol) in methanol (15 mL) was added 2 N lithium hydroxide (8 mL). The mixture was heated to 50° C. overnight. After completion of the reaction, the reaction mixture was concentrated to dryness. Water was added and the pH was adjusted with 2 N hydrochloric acid to pH 2. The precipitated solid was filtered and dried under vacuum to afford 0.2 g (35.48%) of the title compound as a pale brown solid. MS (APCI): 364 (M+H+) for C16H18N4O4S; NMR: δ 1.1 (t, 3H), δ 2.8 (s, 3H), δ 3.07 (s, 3H), δ 7.62 (d, 1H), δ 7.75 (br s, 1H), δ 8.25 (d, 1H), δ 8.82 (s, 1H), δ 9.55 (br s, 1H).

Provenance & Evidence