Реакция #166442

Уравнение реакции

oxalyl chloride

7-(2-methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxylic acid

1-benzyl-3-ethyl-1H-indazol-4-amine

triethylamine

→

N-(1-benzyl-3-ethyl-1H-indazol-4-yl)-7-(2-methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxamide

Выход 18.8%

Растворители

N,N-dimethylformamide

dichloromethane

Условия реакции

Обработка

1. 1
   Температураto warm to ambient temperature
2. 2
   workup.STIRRINGstirred for 16 hours
3. 3
   ДругоеThe mixture was evaporated to dryness under a stream of nitrogen
4. 4
   ДругоеThe resulting residue was purified
5. 5
   Промывкаeluting with 5% methanol in dichloromethane
6. 6
   ДругоеThe material was further purified with a second preparative thin layer chromatography
7. 7
   Промывкаeluting with 8% methanol in chloroform containing 0.5% ammonium hydroxide solution

Методика

To a magnetically stirred suspension of 7-(2-methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxylic acid (32.1 mg, 0.136 mmol) (prepared as in Example 1, steps A-D) in dry dichloromethane (1.5 mL), in a sealed vial, was added dry N,N-dimethylformamide (5 μL). The stirred mixture was cooled to 5° C. using ice bath. A solution of oxalyl chloride (86.8 μL, 0.174 mmol; 2M in dichloromethane) was added and the mixture was stirred for 10 minutes, occasionally allowing the resulting gases to vent. To the resulting solution was added 1-benzyl-3-ethyl-1H-indazol-4-amine (40 mg, 0.159 mmol) and triethylamine (30.2 μL, 0.217 mmol). The mixture was allowed to warm to ambient temperature and stirred for 16 hours. The mixture was evaporated to dryness under a stream of nitrogen. The resulting residue was purified using preparative thin layer chromatography, eluting with 5% methanol in dichloromethane. The material was further purified with a second preparative thin layer chromatography, eluting with 8% methanol in chloroform containing 0.5% ammonium hydroxide solution to provide N-(1-benzyl-3-ethyl-1H-indazol-4-yl)-7-(2-methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxamide (12 mg). MS (APCI), positive scan, m/z=470.3 (M+H).

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