Reacción #69561

Ecuación de reacción

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

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónthe reaction mixture was extracted with ethyl acetate
2. 2
   Secadodried over anhydrous magnesium sulfate
3. 3
   FiltraciónThe mixture was filtered
4. 4
   workup.DISTILLATIONthe solvent in the filtrate was distilled off under reduced pressure
5. 5
   OtroThe residue was purified by HPLC

Procedimiento

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).

Fuente