1-Bromo-2-methylpropane → 4-{[(3,5-dimethyl-4-isoxazolyl)methyl]oxy}-N-[2-methyl-6-(2-oxo-1,3-oxazolidin-3-yl)-3-pyridinyl]-N-(2-methylpropyl)benzenesulfonamide

HRID 594151

Reaktionsgleichung

Reaktionsgleichung von HRID 594151
[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[C:20]([CH3:31])=[N:21][C:22]([N:25]4[CH2:29][CH2:28][O:27][C:26]4=[O:30])=[CH:23][CH:24]=3)(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[C:5]([CH3:32])[O:4][N:3]=1.[CH3:33][C:34](N=C(N(C)C)N(C)C)([CH3:36])[CH3:35].BrCC(C)C>C(#N)C>[CH3:1][C:2]1[C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([N:18]([C:19]3[C:20]([CH3:31])=[N:21][C:22]([N:25]4[CH2:29][CH2:28][O:27][C:26]4=[O:30])=[CH:23][CH:24]=3)[CH2:33][CH:34]([CH3:36])[CH3:35])(=[O:16])=[O:17])=[CH:11][CH:10]=2)=[C:5]([CH3:32])[O:4][N:3]=1

Komponenten

5

Edukt 3

HCID 65551-Bromo-2-methylpropaneHCID 35715812-tert-Butyl-1,1,3,3-tetramethylguanidineHCID 898762884-{[(3,5-dimethyl-4-isoxazolyl)methyl]oxy}-N-[2-methyl-6-(2-oxo-1,3-oxazolidin-3-yl)-3-pyridinyl]benzenesulfonamide

Produkt 1

HCID 721941384-{[(3,5-dimethyl-4-isoxazolyl)methyl]oxy}-N-[2-methyl-6-(2-oxo-1,3-oxazolidin-3-yl)-3-pyridinyl]-N-(2-methylpropyl)benzenesulfonamideAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 4-{[(3,5-dimethyl-4-isoxazolyl)methyl]oxy}-N-[2-methyl-6-(2-oxo-1,3-oxazolidin-3-yl)-3-pyridinyl]benzenesulfonamide (137 mg, 0.299 mmol) and N″-(1,1-dimethylethyl)-N,N,N′,N′-tetramethylguanidine (51 mg, 0.299 mmol) in acetonitrile (2 mL) was added 1-bromo-2-methylpropane (0.065 mL, 0.598 mmol). The reaction vessel was heated at 80° C. for 8 hours. The reaction mixture was then separated between ethyl acetate and saturated sodium bicarbonate solution. The organic phase was washed with brine, dried over magnesium sulphate then concentrated in vacuo. The crude was purified by flash silica (Si) chromatography (0-100% ethyl acetate-cyclohexane gradient) to give the title compound (100 mg) as a white foam. LCMS (2 min, formic) Rt 1.21 min, m/z (ES+) 515 (M+H).

Aufarbeitung

  1. customThe reaction mixture was then separated between ethyl acetate and saturated sodium bicarbonate solution
  2. washThe organic phase was washed with brine
  3. dry with materialdried over magnesium sulphate
  4. concentrationthen concentrated in vacuo
  5. customThe crude was purified by flash silica (Si) chromatography (0-100% ethyl acetate-cyclohexane gradient)

Quellen und Nachweise

ORD-Eintrag
ord-2c117536febd4baa93f9a05462516569
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242972B2

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