1-Bromo-2-methylpropane → 4-((3,5-dimethylisoxazol-4-yl)methoxy)-N-isobutyl-N-(5-methylpyridin-2-yl)benzenesulfonamide

HRID 594148

Reaktionsgleichung

Reaktionsgleichung von HRID 594148
[CH3:1][C:2]1[C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][N:20]=3)(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[C:5]([CH3:26])[O:4][N:3]=1.[C:27](N=C(N(C)C)N(C)C)([CH3:30])([CH3:29])[CH3:28].BrCC(C)C>C(#N)C>[CH3:1][C:2]1[C:6]([CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12]([S:15]([N:18]([CH2:28][CH:27]([CH3:30])[CH3:29])[C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][N:20]=3)(=[O:17])=[O:16])=[CH:13][CH:14]=2)=[C:5]([CH3:26])[O:4][N:3]=1

Komponenten

5

Edukt 3

HCID 65551-Bromo-2-methylpropaneHCID 35715812-tert-Butyl-1,1,3,3-tetramethylguanidineHCID 898762704-((3,5-dimethylisoxazol-4-yl)-methoxy)-N-(5-methylpyridin-2-yl)benzenesulfonamide

Produkt 1

HCID 721960224-((3,5-dimethylisoxazol-4-yl)methoxy)-N-isobutyl-N-(5-methylpyridin-2-yl)benzenesulfonamideAusbeute 4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 4-((3,5-dimethylisoxazol-4-yl)methoxy)-N-(5-methylpyridin-2-yl)benzenesulfonamide (187 mg, 0.5 mmol) in acetonitrile (5 mL) stirred at room temperature, was added 2-(tert-butyl)-1,1,3,3-tetramethylguanidine (0.261 mL, 1.250 mmol). The mixture was stirred at room temperature for 1 hour, then 1-bromo-2-methylpropane (0.190 mL, 1.750 mmol) added. The reaction was then heated by microwaves to 160° C., for 25 minutes. After cooling, dicholormethane (5 mL) was added to the mixture and the organic phase washed with water (5 mL) then separated using a hydrophobic frit. The solvent was removed under a stream of nitrogen and the crude sample purified by mass directed autoprep (ammonium carbonate modifier) to give the title product (8.5 mg). LCMS (3 min, High pH) Rt 1.88 min, m/z (ES+) 430 (M+H).

Aufarbeitung

  1. temperatureThe reaction was then heated by microwaves to 160° C., for 25 minutes
  2. temperatureAfter cooling
  3. additiondicholormethane (5 mL) was added to the mixture
  4. washthe organic phase washed with water (5 mL)
  5. customthen separated
  6. customThe solvent was removed under a stream of nitrogen
  7. customthe crude sample purified by mass

Quellen und Nachweise

ORD-Eintrag
ord-84ca2019465b432baac42525ba1c3256
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242972B2

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