Реакция #67140

Уравнение реакции

sodium iodide

(2R,6S)-2,6-Dimethylmorpholine

4-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]-6-(1H-indol-4-yl)-1-(phenylsulfonyl)-1H-indazole

sodium hydroxide

N,N-diisopropylethylamine

→

title compound

Выход 9.0%

4-(5-{[(2R,6S)-2,6-Dimethyl-4-morpholinyl]methyl}-1,3,4-oxadiazol-2-yl)-6-(1H-indol-4-yl)-1H-indazole

Выход 9.0%

Растворители

Isopropanol

acetonitrile

Условия реакции

Обработка

1. 1
   workup.STIRRINGstirred for 18 h when the mixture
2. 2
   Другоеthe solvent removed under a stream of nitrogen
3. 3
   workup.DISSOLUTIONThe crude product was dissolved in dimethylsulphoxide (0.5 ml)
4. 4
   Другоеpurified by Mass Directed Automated Preparative HPLC (Method F)
5. 5
   Другоеthe solvent was evaporated in vacuo

Методика

(2R,6S)-2,6-Dimethylmorpholine (12.57 mg, 0.11 mmol) and 4-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]-6-(1H-indol-4-yl)-1-(phenylsulfonyl)-1H-indazole (51 mg, 0.104 mmol) were dissolved in acetonitrile (0.5 ml) and N,N-diisopropylethylamine (0.0262 ml, 0.15 mmol) was added, followed by sodium iodide (14.99 mg, 0.1 mmol). The solution was stirred at 70° C. for 18 h and blown to dryness under a stream of nitrogen. Isopropanol (0.5 ml) was added followed by 2M sodium hydroxide (0.5 ml) and stirred for 18 h when the mixture was neutralised and the solvent removed under a stream of nitrogen. The crude product was dissolved in dimethylsulphoxide (0.5 ml) and purified by Mass Directed Automated Preparative HPLC (Method F) and the solvent was evaporated in vacuo using Genevac to give the title compound (4 mg).

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