Cesium carbonate → N-(cyanomethyl)-4-methyl-2-[(4-{[4-(methylsulfonyl)piperazin-1-yl]carbonyl}phenyl)(phenyl)methoxy]pentanamide

HRID 1180383Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1180383
[C:1]([CH2:3][NH:4][C:5](=[O:33])[CH:6]([O:11][CH:12]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:13]1[CH:18]=[CH:17][C:16]([C:19]([N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)=[O:20])=[CH:15][CH:14]=1)[CH2:7][CH:8]([CH3:10])[CH3:9])#[N:2].[CH3:34][S:35](Cl)(=[O:37])=[O:36].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.ClCCl>[C:1]([CH2:3][NH:4][C:5](=[O:33])[CH:6]([O:11][CH:12]([C:13]1[CH:18]=[CH:17][C:16]([C:19]([N:21]2[CH2:22][CH2:23][N:24]([S:35]([CH3:34])(=[O:37])=[O:36])[CH2:25][CH2:26]2)=[O:20])=[CH:15][CH:14]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:7][CH:8]([CH3:10])[CH3:9])#[N:2]

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 31297Methanesulfonyl chlorideHCID 85089179N-(cyanomethyl)-4-methyl-2-{phenyl[4-(piperazin-1-ylcarbonyl)phenyl]methoxy}pentanamide

Produkt 1

HCID 86605380N-(cyanomethyl)-4-methyl-2-[(4-{[4-(methylsulfonyl)piperazin-1-yl]carbonyl}phenyl)(phenyl)methoxy]pentanamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of N-(cyanomethyl)-4-methyl-2-{phenyl[4-(piperazin-1-ylcarbonyl)phenyl]methoxy}pentanamide from example 17, step 7 (102 mg, 0.23 mmol) in DMF (1 mL), was added methyl sulfonyl chloride (27 μL, 0.35 mmol) and cesium carbonate (91 mg, 0.28 mmol). The mixture was aged for 2 hours under nitrogen atmosphere and was diluted with dichloromethane. The resulting mixture was filtered over celite and concentrated under reduced pressure. The crude residue was chromatographed on silica gel using 1% NH4OH and 9% methanol in dichloromethane to afford the title compound.

Aufarbeitung

  1. filtrationThe resulting mixture was filtered over celite and
  2. concentrationconcentrated under reduced pressure
  3. customThe crude residue was chromatographed on silica gel using 1% NH4OH and 9% methanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-e3d7f9a26582487896f61746f50fa1ff
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07279478B2

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