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With triethylamine; In dimethyl sulfoxide; at 140℃; for 0.5h;Microwave irradiation;
Example-88 (6-Methyl-5-nitro-2-pyridin-2-ylamino)-butionic methyl ester 6-chloro-3-nitro-2-picoline (600 mg, 3.5 mmol) was coupled with glycine methyl ester hydrochloride (880 mg, 7 mmol), triethylamine (1.5 ml, 10.5 mmol) in DMSO 3 mL at 140 °C for 30 min in microwave (Parameters : high absorbance, fixed holding time, pre- stirring 25 seconds). The crude mixture was treated with a saturated aqueous solution of NH4Cl. The aqueous solution of was extracted with EtOAc, washed with water and brine. The crude product was purified on a silica column with CH2Cl2-MeOH as mobile phase. This gave 39 mg (51percent) of 580 mg (74percent) of (6-methyl-5-nitro-2-pyridin-2-ylarcino)- budonic methyl ester as a yellow solid.
Example 1: Synthesis of [l-(l,4-dimethyl-lH-indol-3-ylmethyl)-2,4-dioxo-l,4-dihydro-2H- pyrido[3,4-rf]pyrimidin-3-yl]-acetic acid; To a solution of lOOmg of 3-amino-isonicotinic acid in pyridine (2.5 mL) is added 117 mg of l,l'-carbonyldiimidazole and the mixture is stirred for 20 min at 55 0C. Then the mixture is cooled to room temperature and 91 mg of glycine methylester hydrochloride is added and the resulting mixture is stirred for 30 min at 55 0C and 1 h at room temperature. Then the solvent is removed under vaccum and the residue is purified by flash chromatography on silica gel to give 100 mg (66 percent) of [(3-amino-pyridine-4-carbonyl)-amino]-acetic acid methyl ester.
methyl N-(5-iodo-3-nitropyridin-2-yl)glycinate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
11.1 g
With triethylamine; In ethanol; for 20.0h;Reflux;
A) methyl N-(5-iodo-3-nitropyridin-2-yl)glycinate To a solution of <strong>[426463-05-0]2-chloro-5-iodo-3-nitropyridine</strong> (12.0 g) in ethanol (200 mL) were added methyl glycinate hydrochloride (10.6 g) and triethylamine (11.8 mL) at room temperature. The reaction mixture was heated at reflux for 20 hr, and the solvent was evaporated under reduced pressure. To the residue was added water, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was crystallized from hexane/ethyl acetate to give the title compound (11.1 g). MS (API+): [M+H]+ 338.0.
Glycine methyl ester hydrochloride (925 mg, 7.37 mmol, 1.1 eq) was added to a solution of triethylamine (1.07 mL, 8.04 mmol, 1.2 eq) in toluene (20 mL). The reaction mixture was stirred for 30 minutes on 3 A molecular sieves. Then <strong>[54221-96-4]6-methoxy-2-pyridinecarboxaldehyde</strong> (0.92 g, 6.70 mmol, 1.0 eq) was added and the reaction mixture was stirred at room temperature overnight. The reaction mixture was filtered, diluted with toluene and cooled to 0° C., and used in the next step without further purification.
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