Water → HCID 9932747, compound

Participants

Reaction Conditions

Reaction Steps

Eighteen mg of the 6-(2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl-2-(2-carboxyphenyl)-4-quinolinecarboxylic acid obtained in Example 17 were dissolved in 5 ml of quinoline. After adding 0.5 ml of conc. sulfuric acid, the mixture was heated at 170° C. for 1 hour. Then the reaction mixture was poured into water, made alkaline by adding sodium carbonate and washed with toluene. The aqueous layer was neutralized with 3M hydrochloric acid until a precipitate was formed. Then the precipitate was collected by filtration and purified by flash chromatography on silica gel with the use of chloroform/methanol. Thus 12 mg of 2-{6-[(2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl]quinolin-2-yl}benzoic acid were obtained. NMR (270 MHz, CDCl3): δ 7.5-8.2 (m,8H); 7.4 (s,1H); 7.0 (s,1H); 5.7 (s,2H); 2.8 (q,J=8Hz,2H); 2.7 (s,3H); 2.6 (s,3H); 1.7 (t,J=8Hz,3H).

Provenance & Evidence