Sodium hydride → 2-chloro-N-(3,5-dimethylpyridin-2-yl)-N-isobutyl-4-((tetrahydro-2H-pyran-4-yl)methoxy)benzenesulfonamide

HRID 594152Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 594152
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.[Cl:9][C:10]1[CH:15]=[C:14](F)[CH:13]=[CH:12][C:11]=1[S:17]([N:20]([C:25]1[C:30]([CH3:31])=[CH:29][C:28]([CH3:32])=[CH:27][N:26]=1)[CH2:21][CH:22]([CH3:24])[CH3:23])(=[O:19])=[O:18].[H-].[Na+]>CS(C)=O>[Cl:9][C:10]1[CH:15]=[C:14]([O:1][CH2:2][CH:3]2[CH2:8][CH2:7][O:6][CH2:5][CH2:4]2)[CH:13]=[CH:12][C:11]=1[S:17]([N:20]([C:25]1[C:30]([CH3:31])=[CH:29][C:28]([CH3:32])=[CH:27][N:26]=1)[CH2:21][CH:22]([CH3:23])[CH3:24])(=[O:19])=[O:18]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 2773573(Oxan-4-yl)methanolHCID 898760522-chloro-N-(3,5-dimethylpyridin-2-yl)-4-fluoro-N-isobutylbenzenesulfonamide

Produkt 1

HCID 721942782-chloro-N-(3,5-dimethylpyridin-2-yl)-N-isobutyl-4-((tetrahydro-2H-pyran-4-yl)methoxy)benzenesulfonamideAusbeute 48,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To a stirred solution of 4-(hydroxylmethyl)tetrahydro-2H-pyran (2.63 mg, 0.023 mmol) and 2-chloro-N-(3,5-dimethylpyridin-2-yl)-4-fluoro-N-isobutylbenzenesulfonamide (8.4 mg, 0.023 mmol) in dimethyl sulfoxide (200 μL) at room temperature was added sodium hydride (60% wt in mineral oil) (0.906 mg, 0.023 mmol) and the reaction stirred for 2 hours. The reaction was quenched with methanol (2 mL) and water (2 mL), then the solvents evaporated in vacuo. The crude product was purified by flash silica (Si) chromatography (25% ethyl acetate-cyclohexane gradient) to give the title compound (5.2 mg). LCMS (2 min, High pH) Rt 1.48 min, m/z (ES+) 468 (M+H).

Aufarbeitung

  1. customThe reaction was quenched with methanol (2 mL) and water (2 mL)
  2. customthe solvents evaporated in vacuo
  3. customThe crude product was purified by flash silica (Si) chromatography (25% ethyl acetate-cyclohexane gradient)

Quellen und Nachweise

ORD-Eintrag
ord-623da59365e54c6c893e14d6e6078a64
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242972B2

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