반응 #78481

반응 방정식

1-methyl-2-[(4-cyanophenyl)oxymethyl]-5-carboxyimidazo[4,5-b]pyridine

N-methylmorpholine

O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate

methyl N-(2-pyridyl)-3-aminopropionate

→

1-Methyl-2-[(4-cyanophenyl)oxymethyl]imidazo[4,5-b]pyridin-5-yl-carboxlic acid-N-(2-pyridyl)-N-(2-methoxycarbonylethyl)amide

용매

dimethylformamide

dimethylformamide

반응 조건

후처리

1. 1
   기타was obtained
2. 2
   workup.WAITAfter 12 hours at room temperature
3. 3
   추출After extracting 3 times with ethyl acetate
4. 4
   세척the combined organic extracts were washed with a saline solution
5. 5
   건조dried over sodium sulfate
6. 6
   기타evaporated down
7. 7
   기타The residue obtained
8. 8
   기타was chromatographed on silica gel with dichloromethane/ethanol (90:1 to 25:1)

실험 절차

308 mg (1.0 mmol) of 1-methyl-2-[(4-cyanophenyl)oxymethyl]-5-carboxyimidazo[4,5-b]pyridine were suspended in 5 mL of dimethylformamide and mixed with 303 mg (3.0 mmol) of N-methylmorpholine and 321 mg (1.0 mmol) of O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate. After 10 minutes at room temperature, a solution of 215 mg (1.2 mmol) of methyl N-(2-pyridyl)-3-aminopropionate in 2 mL of dimethylformamide was added, whereupon a clear solution was obtained. After 12 hours at room temperature, the reaction solution was stirred into ice-water. After extracting 3 times with ethyl acetate, the combined organic extracts were washed with a saline solution, dried over sodium sulfate, and evaporated down. The residue obtained was chromatographed on silica gel with dichloromethane/ethanol (90:1 to 25:1). Yield: 165 mg of white powder (35% of theory), C25H12N6O4 (407.50); melting point: 139° C.-140° C.

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