Hydrochloric Acid → HCID 18663762, compound

Participants

Reaction Steps

In 35 ml of methanol were dissolved 3.6 g (6.9 mmol) of methyl 2-(2-methoxycarboxyphenyl)-3-methyl-6-[(2-butyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl]-4-quinolinecarboxylate obtained in the method described in Example 36. Then, 14 ml of a 0.5N aqueous solution of sodium hydroxide were added thereto and the mixture was stirred at room temperature for 16 hours. After the reaction mixture was neutralized with 1N hydrochloric acid, methanol was distilled off and 35 ml of water were added to the residue. The mixture was extracted with 30 ml of methylene chloride and the aqueous layer was acidified with 2N hydrochloric acid under stirring. The resulting precipitate was collected by filtration, washed with water and dried to give 1.8 g of 2-(2-methoxycarboxyphenyl)-3-methyl-6-[(2-butyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl]-4-quinolinecarboxylic acid. NMR (270 MHz, CDCl3) δ 8.3 (m,1H); 8.0-8.1 (m,3H); 7.79 (d,J=7.8Hz,1H); 7.1-7.6 (m,5H); 5.71 (s,2H); 3.5 (s,3H); 2.87 (t,J=7.8Hz,2H); 2.6 (s,3H); 1.80-1.88 (m,2H); 1.4-1.48 (m,2H); 0.92 (t,J=7.3Hz,3H).

Provenance & Evidence