Triethylamine → N-{2-[(2,3-Difluorobenzyl)thio]-6-methoxypyrimidin-4-yl}-3-morpholin-4-ylazetidine-1-sulfonamide

温度

50 °C

A solution of N-{2-[(2,3-difluorobenzyl)thio]-6-methoxypyrimidin-4-yl}-3-hydroxyazetidine-1-sulfonamide (the product from example 109) (0.28 g) in DCM (10 ml) was treated with triethylamine (0.8 ml) and methanesulfonylchloride (0.9 ml) under nitrogen. After heating the mixture at 50° C. for 16 h the reaction mixture was partitioned between DCM and aqueous NaHCO3. The organic extracts were dried (MgSO4), filtered and the solvent evaporated under reduced pressure. To a solution of the resulting residue in MeOH (10 mL) and morpholine (8 ml) K2CO3 (0.19 g) was added and heated at 80° C. for 16 h. The reaction mixture was then partitioned between EtOAc and H2O The organic extracts were washed with brine, dried (MgSO4), filtered and the solvent evaporated under reduced pressure. The residue was purified by reverse phase HPLC (symmetry as the stationary phase and NH4OAc/acetonitrile as the mobile phase) then titurated with Et2O to give the title compound as a white solid.

1. customwas partitioned between DCM and aqueous NaHCO3
2. dry with materialThe organic extracts were dried (MgSO4)
3. filtrationfiltered
4. customthe solvent evaporated under reduced pressure
5. additionTo a solution of the resulting residue in MeOH (10 mL) and morpholine (8 ml) K2CO3 (0.19 g) was added
6. temperatureheated at 80° C. for 16 h
7. customThe reaction mixture was then partitioned between EtOAc and H2O The organic extracts
8. washwere washed with brine
9. dry with materialdried (MgSO4)
10. filtrationfiltered
11. customthe solvent evaporated under reduced pressure
12. customThe residue was purified by reverse phase HPLC (symmetry as the stationary phase and NH4OAc/acetonitrile as the mobile phase)

ORDレコード

ord-bcd6aad839a548e5a6a41abad6944317

出典データセット

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07838675B2