Sodium hydride → N-isobutyl-N-(5-isopropylpyridin-2-yl)-4-((tetrahydro-2H-pyran-4-yl)methoxy)benzenesulfonamide

HRID 594161Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 594161
F[C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:12]2[CH:17]=[CH:16][C:15]([CH:18]([CH3:20])[CH3:19])=[CH:14][N:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[O:25]1[CH2:30][CH2:29][CH:28]([CH2:31][OH:32])[CH2:27][CH2:26]1.[H-].[Na+]>CN(C)C=O>[CH2:21]([N:11]([C:12]1[CH:17]=[CH:16][C:15]([CH:18]([CH3:20])[CH3:19])=[CH:14][N:13]=1)[S:8]([C:5]1[CH:6]=[CH:7][C:2]([O:32][CH2:31][CH:28]2[CH2:29][CH2:30][O:25][CH2:26][CH2:27]2)=[CH:3][CH:4]=1)(=[O:10])=[O:9])[CH:22]([CH3:24])[CH3:23]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 2773573(Oxan-4-yl)methanolHCID 898760314-fluoro-N-isobutyl-N-(5-isopropylpyridin-2-yl)benzenesulfonamide

Produkt 1

HCID 72194555N-isobutyl-N-(5-isopropylpyridin-2-yl)-4-((tetrahydro-2H-pyran-4-yl)methoxy)benzenesulfonamideAusbeute 44,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-fluoro-N-isobutyl-N-(5-isopropylpyridin-2-yl)benzenesulfonamide (30 mg, 0.086 mmol) was dissolved in N,N-dimethylformamide (DMF) (3 mL) and to this solution was added (tetrahydro-2H-pyran-4-yl)methanol (12 mg, 0.10 mmol) and sodium hydride (2 mg, 0.10 mmol, 60% wt in mineral oil). The reaction was stirred under nitrogen for 2 hours at room temperature. The reaction was quenched then concentrated in vacuo and the crude product extracted to the organic phase of an aqueous work up between ethyl acetate and water. The organic phase was passed through a hydrophobic frit, concentrated in vacuo and purified by mass directed autoprep (formic acid modifier) to give the title compound (17 mg). LCMS (2 min, formic) Rt 1.41 min, m/z (ES+) 447 (M+H).

Aufarbeitung

  1. customThe reaction was quenched
  2. concentrationthen concentrated in vacuo
  3. extractionthe crude product extracted to the organic phase of an aqueous work up between ethyl acetate and water
  4. concentrationconcentrated in vacuo
  5. custompurified by mass

Quellen und Nachweise

ORD-Eintrag
ord-2208adb7fdee4a5b8a923081b7d3b575
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242972B2

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