Cesium carbonate → 3-Fluoro-4-{[(1S*,2R*)-2-(1-methyl-1H-pyrazol-5-yl)cyclopentyl]oxy}-N-(1,3-thiazol-2-yl)benzenesulfonamide

HRID 337734Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 337734
[F:1][C:2]1[CH:3]=[C:4]([S:20]([NH2:23])(=[O:22])=[O:21])[CH:5]=[CH:6][C:7]=1[O:8][C@H:9]1[CH2:13][CH2:12][CH2:11][C@@H:10]1[C:14]1[N:18]([CH3:19])[N:17]=[CH:16][CH:15]=1.Br[C:25]1[S:26][CH:27]=[CH:28][N:29]=1.CN[C@@H]1CCCC[C@H]1NC.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.[Cu](I)I>[F:1][C:2]1[CH:3]=[C:4]([S:20]([NH:23][C:25]2[S:26][CH:27]=[CH:28][N:29]=2)(=[O:21])=[O:22])[CH:5]=[CH:6][C:7]=1[O:8][C@H:9]1[CH2:13][CH2:12][CH2:11][C@@H:10]1[C:14]1[N:18]([CH3:19])[N:17]=[CH:16][CH:15]=1

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 764302-BromothiazoleHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 899632593-Fluoro-4-{[(1S*,2R*)-2-(1-methyl-1H-pyrazol-5-yl)cyclopentyl]oxy}benzenesulfonamide

Produkt 1

HCID 899636633-Fluoro-4-{[(1S*,2R*)-2-(1-methyl-1H-pyrazol-5-yl)cyclopentyl]oxy}-N-(1,3-thiazol-2-yl)benzenesulfonamideAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717Copper iodideKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of the 3-fluoro-4-{[(1S*,2R*)-2-(1-methyl-1H-pyrazol-5-yl)cyclopentyl]oxy}benzenesulfonamide (0.07 g, 0.21 mmol) prepared in Example 16c, 2-bromothiazole (0.07 g, 0.41 mmol), copper iodide (0.01 g, 0.04 mmol), trans-N,N′-dimethylcyclohexane-1,2-diamine (0.01 g, 0.09 mmol) and cesium carbonate (0.20 g, 0.62 mmol) in DMF (2.0 mL) was stirred at 120° C. for 20 hours under the nitrogen atmosphere. After allowing to cool, the reaction solution was vacuum concentrated, and the residue was purified with HPLC to yield the title compound (75 mg, 86%) as a colorless solid.

Aufarbeitung

  1. temperatureto cool
  2. concentrationconcentrated
  3. customthe residue was purified with HPLC

Quellen und Nachweise

ORD-Eintrag
ord-aece0d123fa14c5fa4b22a9eede1b510
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889741B2

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