Réaction #162064
ord-c2b29f0fc7b041fe86c0a451d685ed86
Équation de réaction
Réactifs
Réactifs
Solvants
Conditions de réaction
Traitement
- 1Autrereaction
- 2Autrethe solution evaporated to dryness
- 3workup.DISSOLUTIONThe resulting residue was dissolved in methanol (2 mL)
- 4workup.ADDITIONthen treated with 25% sodium methoxide/methanol (0.5 mL)
- 5Températureheated at 60° C. in sealed tube for 10 minutes
- 6AutreThe solution was quenched with aqueous saturated NH4Cl solution (0.5 mL)
- 7Autrethen evaporated to dryness
- 8workup.DISSOLUTIONThe resulting residue was dissolved in DMSO
- 9Autrepurified by reverse phase HPLC (ammonium formate buffer)
Mode opératoire
To a stirred solution of N-(azetidin-3-yl)-2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-amine hydrochloride, 6c, (0.03 g, 0.06 mmol) in dichloromethane (1 mL) was added iPr2NEt (0.33 μL, 1.90 mmol) followed by cyclopentylmethanesulfonyl chloride (0.01 g, 0.06 mmol). The resulting mixture was stirred 30 minutes at room temperature at which time LCMS showed complete reaction. Morpholine (0.20 mL) was added and the solution evaporated to dryness. The resulting residue was dissolved in methanol (2 mL) then treated with 25% sodium methoxide/methanol (0.5 mL) and heated at 60° C. in sealed tube for 10 minutes. The solution was quenched with aqueous saturated NH4Cl solution (0.5 mL) then evaporated to dryness. The resulting residue was dissolved in DMSO and purified by reverse phase HPLC (ammonium formate buffer) to afford 27.4 mg (88% yield) of the desired product, 469, as a solid. LCMS RT=3.1 min, ES+465.