反応 #69561

反応方程式

hydrogencarbonate

4-({cyclopropylmethyl-[3-(2,6-dimethoxy-4-methoxymethyl-phenyl)-6-methoxy-pyrazolo[5,1-b][1,3]thiazol-7-yl]-amino}-methyl)-tetrahydro-pyran-4-ol

diethylaminosulfur trifluoride

→

cyclopropylmethyl-[3-(2,6-dimethoxy-4-methoxymethyl-phenyl)-6-methoxy-pyrazolo[5,1-b][1,3]thiazol-7-yl]-(4-fluoro-tetrahydro-pyran-4-ylmethyl)-amine

cyclopropylmethyl-(3,6-dihydro-2H-pyran-4-ylmethyl)-[3-(2,6-dimethoxy-4-methoxymethyl-phenyl)-6-methoxy-pyrazolo[5,1-b][1,3]thiazol-7-yl]-amine

溶媒

dichloromethane

反応条件

後処理

1. 1
   抽出the reaction mixture was extracted with ethyl acetate
2. 2
   乾燥dried over anhydrous magnesium sulfate
3. 3
   ろ過The mixture was filtered
4. 4
   workup.DISTILLATIONthe solvent in the filtrate was distilled off under reduced pressure
5. 5
   その他The residue was purified by HPLC

実験手順

To a dichloromethane (4 mL) solution of 4-({cyclopropylmethyl-[3-(2,6-dimethoxy-4-methoxymethyl-phenyl)-6-methoxy-pyrazolo[5,1-b][1,3]thiazol-7-yl]-amino}-methyl)-tetrahydro-pyran-4-ol (64.5 mg, 0.124 mmol) was added dropwise diethylaminosulfur trifluoride (DAST) (24.6 μL, 0.186 mmol), and the mixture was stirred for five minutes. After the reaction was completed, a saturated aqueous solution of hydrogencarbonate was added to the reaction mixture, and the reaction mixture was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The mixture was filtered, and then the solvent in the filtrate was distilled off under reduced pressure. The residue was purified by HPLC to obtain cyclopropylmethyl-[3-(2,6-dimethoxy-4-methoxymethyl-phenyl)-6-methoxy-pyrazolo[5,1-b][1,3]thiazol-7-yl]-(4-fluoro-tetrahydro-pyran-4-ylmethyl)-amine (8.9 mg, 0.017 mmol) and cyclopropylmethyl-(3,6-dihydro-2H-pyran-4-ylmethyl)-[3-(2,6-dimethoxy-4-methoxymethyl-phenyl)-6-methoxy-pyrazolo[5,1-b][1,3]thiazol-7-yl]-amine (1.3 mg, 0.003 mmol).

出典