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Cesium carbonate → N-[2-[[(2,3-difluorophenyl)methyl]thio]-6-[(2,2-dimethyl-1,3-dioxan-5-yl)methyl]-4-pyrimidinyl]azetidine-1-sulphonamide

HRID 1024837
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1024837
Cl[C:2]1[CH:7]=[C:6]([CH2:8][CH:9]2[CH2:14][O:13][C:12]([CH3:16])([CH3:15])[O:11][CH2:10]2)[N:5]=[C:4]([S:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:20]=2[F:26])[N:3]=1.[N:27]1([S:31]([NH2:34])(=[O:33])=[O:32])[CH2:30][CH2:29][CH2:28]1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:26][C:20]1[C:21]([F:25])=[CH:22][CH:23]=[CH:24][C:19]=1[CH2:18][S:17][C:4]1[N:3]=[C:2]([NH:34][S:31]([N:27]2[CH2:30][CH2:29][CH2:28]2)(=[O:33])=[O:32])[CH:7]=[C:6]([CH2:8][CH:9]2[CH2:14][O:13][C:12]([CH3:16])([CH3:15])[O:11][CH2:10]2)[N:5]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 450805661-AzetidinesulfonamideHCID 866198634-Chloro-2-[[(2,3-difluorophenyl)methyl]thio]-6-[(2,2-dimethyl-1,3-dioxan-5-yl)methyl]pyrimidine

Produkt 1

HCID 53628340N-[2-[[(2,3-difluorophenyl)methyl]thio]-6-[(2,2-dimethyl-1,3-dioxan-5-yl)methyl]-4-pyrimidinyl]azetidine-1-sulphonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564
Bis(dibenzylideneacetone)palladium
Katalysator
HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of the product of step i) (109 mg), tris(dibenzylideneacetone)dipalladium(0) (14 mg), azetidine-1-sulphonamide (145 mg), 2-dicyclohexyl-phosphino-2′,4′,6′-triisopropyl,1,1′-biphenyl (XPHOS) (14 mg) and cesium carbonate (120 mg) in anhydrous dioxane (2.3 ml) was heated at 100° C. for 45 min. The reaction mixture was partitioned between ethyl acetate and water. Acetic acid (0.2 ml) was added and the separated organic phase was washed with water and brine, dried (MgSO4) and the solvent evaporated under reduced pressure. The residue was purified by flash silica-gel chromatography eluting with 40% ethyl acetate in iso-hexane to give the sub-title compound as a yellow viscous oil. Yield: 78 mg.

Aufarbeitung

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. additionAcetic acid (0.2 ml) was added
  3. washthe separated organic phase was washed with water and brine
  4. dry with materialdried (MgSO4)
  5. customthe solvent evaporated under reduced pressure
  6. customThe residue was purified by flash silica-gel chromatography
  7. washeluting with 40% ethyl acetate in iso-hexane

Quellen und Nachweise

ORD-Eintrag
ord-6f39fa6155c6460889645e437c81ebb2
Quelldatensatz
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08722883B2

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