4-Hydroxymethylpyridine → N-isobutyl-N-(6-methoxypyridin-2-yl)-4-(pyridin-4-ylmethoxy)benzenesulfonamide

HRID 594156Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 594156
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][OH:8])=[CH:3][CH:2]=1.F[C:10]1[CH:15]=[CH:14][C:13]([S:16]([N:19]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[N:21]=2)(=[O:18])=[O:17])=[CH:12][CH:11]=1.[H-].[Na+]>CN(C)C=O>[CH2:28]([N:19]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[N:21]=1)[S:16]([C:13]1[CH:14]=[CH:15][C:10]([O:8][CH2:7][C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)=[CH:11][CH:12]=1)(=[O:18])=[O:17])[CH:29]([CH3:31])[CH3:30]

Komponenten

5

Edukt 3

HCID 114724-HydroxymethylpyridineHCID 24758Sodium hydrideHCID 898763574-fluoro-N-isobutyl-N-(6-methoxypyridin-2-yl)benzenesulfonamide

Produkt 1

HCID 72194422N-isobutyl-N-(6-methoxypyridin-2-yl)-4-(pyridin-4-ylmethoxy)benzenesulfonamideAusbeute 26,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Pyridin-4-ylmethanol (20.22 mg, 0.185 mmol) and 4-fluoro-N-isobutyl-N-(6-methoxypyridin-2-yl)benzenesulfonamide (62.7 mg, 0.185 mmol) were dissolved in N,N-dimethylformamide (DMF) (3 mL) and sodium hydride (7.41 mg, 0.185 mmol, 60% wt in mineral oil) added. Reaction left to stir at room temperature, under nitrogen, for 3 hours. The reaction was then quenched by adding water (2 mL). The mixture was concentrated in vacuo and the product extracted to the organic phase of an aqueous work up between ethyl acetate and water. The organic phase was dried by passing it through a hydrophobic frit, concentrated and then purified by mass directed autoprep (formic acid modifier), to give the title compound (21.2 mg). LCMS (2 min, formic) Rt 1.05 min, m/z (ES+) 428 (M+H).

Aufarbeitung

  1. customReaction
  2. waitleft
  3. customThe reaction was then quenched
  4. additionby adding water (2 mL)
  5. concentrationThe mixture was concentrated in vacuo
  6. extractionthe product extracted to the organic phase of an aqueous work up between ethyl acetate and water
  7. customThe organic phase was dried
  8. concentrationconcentrated
  9. custompurified by mass

Quellen und Nachweise

ORD-Eintrag
ord-be83ba92e3ba4af4a1704e5deb9d6574
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242972B2

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