Reaktion #162063
ord-4345c0018ae44ee0b8979a71e67f49e1
Reaktionsgleichung
Edukte
Reagenzien
Lösungsmittel
Reaktionsbedingungen
Aufarbeitung
- 1Sonstigereaction
- 2Sonstigethe 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)
- 5Temperaturheated at 60° C. in sealed tube for 10 minutes
- 6SonstigeThe resulting solution was quenched with aqueous saturated NH4Cl solution (0.5 mL)
- 7Sonstigethen evaporated to dryness
- 8workup.DISSOLUTIONThe resulting residue was dissolved in DMSO
- 9Sonstigepurified by reverse phase HPLC (ammonium formate buffer)
Vorschrift
To a stirred suspension of N-(azetidin-3-yl)-2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-amine hydrochloride, 6c, (0.055 g, 0.110 mmol) in THF (1 mL) was added iPr2NEt (0.300 mL, 1.720 mmol) followed by propane-1-sulfonyl chloride (0.012 mL, 0.108 mmol). The resulting homogenous light yellow solution mixture was heated at 50° C. for one hour 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 resulting 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 19.8 mg (43% yield) of the desired product, 423, as a solid.