Cesium carbonate → N-[2-[[(2,3-difluorophenyl)methyl]thio]-6-[(1R)-1-methyl-2-(triphenylmethoxy)ethoxy]-4-pyrimidinyl]-4-pyridinesulfonamide

HRID 2388746Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2388746
[N:1]1[CH:6]=[CH:5][C:4]([S:7]([NH2:10])(=[O:9])=[O:8])=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:18]1[CH:23]=[C:22]([O:24][C@H:25]([CH3:47])[CH2:26][O:27][C:28]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:21]=[C:20]([S:48][CH2:49][C:50]2[CH:55]=[CH:54][CH:53]=[C:52]([F:56])[C:51]=2[F:57])[N:19]=1>O1CCOCC1.C(Cl)Cl.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:57][C:51]1[C:52]([F:56])=[CH:53][CH:54]=[CH:55][C:50]=1[CH2:49][S:48][C:20]1[N:19]=[C:18]([NH:10][S:7]([C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH:23]=[C:22]([O:24][C@H:25]([CH3:47])[CH2:26][O:27][C:28]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)([C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[N:21]=1

Komponenten

7

Edukt 3

HCID 10796Cesium carbonateHCID 12383449Pyridine-4-sulfonamide2×HCID 536283454-chloro-2-[[(2,3-difluorophenyl)methyl]thio]-6-[(1R)-1-methyl-2-(triphenylmethoxy)ethoxy]-pyrimidine2×

Produkt 1

HCID 53628344N-[2-[[(2,3-difluorophenyl)methyl]thio]-6-[(1R)-1-methyl-2-(triphenylmethoxy)ethoxy]-4-pyrimidinyl]-4-pyridinesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 4-pyridinesulfonamide (the product from step i) (0.21 g), tris(dibenzylideneacetone)dipalladium (0) (50 mg), 2-dicyclohexylphosphino-2′,4′,6′-tri-isopropyl-1,r-biphenyl (XPHOS) (50 mg), cesium carbonate (0.66 g) and 4-chloro-2-[[(2,3-difluorophenyl)methyl]thio]-6-[(1R)-1-methyl-2-(triphenylmethoxy)ethoxy]-pyrimidine (the product from step iii) (0.40 g) in dioxane (20 mL) was heated at reflux in a microwave at 100° C., 300 W, open vessel with cooling for 3 h. The reaction mixture was diluted with DCM, filtered through arbocel and the filtrate evaporated. The residue was purified by reverse phase HPLC using a TFA (0.2%)/MeCN system to give the title compound as a yellow solid. Yield: 0.21 g.

Aufarbeitung

  1. temperaturewas heated
  2. temperature300 W, open vessel with cooling for 3 h
  3. filtrationfiltered through arbocel
  4. customthe filtrate evaporated
  5. customThe residue was purified by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-958d5a6d916148dabe01fe91e837cfd0
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08269002B2

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