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

HRID 2388895
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2388895
[F:1][C:2]1[C:26]([F:27])=[CH:25][CH:24]=[CH:23][C:3]=1[CH2:4][S:5][C:6]1[N:11]=[C:10]([NH:12][S:13]([N:16]2[CH2:19][CH:18](O)[CH2:17]2)(=[O:15])=[O:14])[CH:9]=[C:8]([O:21][CH3:22])[N:7]=1.[CH2:28]([N:30](CC)[CH2:31][CH3:32])[CH3:29].CS(Cl)(=O)=[O:37]>C(Cl)Cl>[F:1][C:2]1[C:26]([F:27])=[CH:25][CH:24]=[CH:23][C:3]=1[CH2:4][S:5][C:6]1[N:11]=[C:10]([NH:12][S:13]([N:16]2[CH2:17][CH:18]([N:30]3[CH2:31][CH2:32][O:37][CH2:29][CH2:28]3)[CH2:19]2)(=[O:15])=[O:14])[CH:9]=[C:8]([O:21][CH3:22])[N:7]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59558820N-{2-[(2,3-Difluorobenzyl)thio]-6-methoxypyrimidin-4-yl}-3-hydroxyazetidine-1-sulfonamide2×

Produkt 1

HCID 59558807N-{2-[(2,3-Difluorobenzyl)thio]-6-methoxypyrimidin-4-yl}-3-morpholin-4-ylazetidine-1-sulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

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.

Aufarbeitung

  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
  8. washThe organic extracts were 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)

Quellen und Nachweise

ORD-Eintrag
ord-4f86340a4ada4ab4a066c58c4c0dae68
Quelldatensatz
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08269002B2

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