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With hydrogenchloride; potassium permanganate; sodium carbonate In water
Step 1004b: Preparation of 3H-imidazo[4,5-b]pyridine-2-carboxylic Acid. To a boiling solution of KMnO4 (0.38 g, 2.4 mmol) in water (8 mL), a boiling solution of 3H-imidazo[4,5-b]pyridin-2-ylmethanol (0.20 g, 1.4 mmol) and Na2CO3 (0.19 g, 1.5 mmol) in water (6 mL) is added. The resulting mixture is heated at reflux for 4 hr. The hot mixture is filtered, the filtrate is cooled to rt, and the pH adjusted to 2 using conc. HCl. The resulting precipitate is collected by vacuum filtration to afford 3H-imidazo[4,5-b]pyridine-2-carboxylic acid in 100percent yield: MS for C7H5N3O2: m/z 164 (M+H)+.
With sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In hydrogenchloride; methanol; diethyl ether; N,N-dimethyl-formamide; isopropyl alcohol;
Step 1004c: Coupling. To <strong>[97640-15-8]3H-imidazo[4,5-b]pyridine-2-carboxylic acid</strong> (90 mg, 0.55 mmol) in DMF (4 mL) is added (R)-(+)-3-aminoquinuclidine dihydrochloride (0.11 g, 0.56 mmol), DIEA (0.25 g, 0.35 mL, 1.9 mmol) and HATU (0.21 g, 0.56 mmol). The mixture is stirred overnight at rt, diluted with CH2Cl2 (50 mL) and washed with 1 N NaOH (2*50 mL) followed by sat. aq. NaHCO3 (50 mL). The material is purified by passage through acidic ion exchange resin. The free base is taken up in 3 M HCl/MeOH (10 mL) and stirred for 1.5 hr. Isopropanol and Et2O are added and the solid is isolated by vacuum filtration to afford Example 1004 in 57% yield. MS for C14H17N5O: 272 (M+H)+.
With hydrogenchloride; potassium permanganate; sodium carbonate; In water;
Step 1004b: Preparation of 3H-imidazo[4,5-b]pyridine-2-carboxylic Acid. To a boiling solution of KMnO4 (0.38 g, 2.4 mmol) in water (8 mL), a boiling solution of 3H-imidazo[4,5-b]pyridin-2-ylmethanol (0.20 g, 1.4 mmol) and Na2CO3 (0.19 g, 1.5 mmol) in water (6 mL) is added. The resulting mixture is heated at reflux for 4 hr. The hot mixture is filtered, the filtrate is cooled to rt, and the pH adjusted to 2 using conc. HCl. The resulting precipitate is collected by vacuum filtration to afford 3H-imidazo[4,5-b]pyridine-2-carboxylic acid in 100% yield: MS for C7H5N3O2: m/z 164 (M+H)+.
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