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1-Bromo-2-methylpropane → 4-((3,5-dimethylisoxazol-4-yl)-methoxy)-N-isobutyl-N-(6-methoxypyridazin-3-yl)benzenesulfonamide

HRID 594153
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 594153
[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[N:20]=[N:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=3)(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[C:5]([CH3:27])[O:4][N:3]=1.[CH3:28][C:29](N=C(N(C)C)N(C)C)([CH3:31])[CH3:30].BrCC(C)C>C(#N)C.CO>[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:29]([CH3:31])[CH3:30])[C:19]3[N:20]=[N:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=3)(=[O:17])=[O:16])=[CH:13][CH:14]=2)=[C:5]([CH3:27])[O:4][N:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 65551-Bromo-2-methylpropaneHCID 35715812-tert-Butyl-1,1,3,3-tetramethylguanidineHCID 1179259484-{[(3,5-dimethyl-4-isoxazolyl)methyl]oxy}-N-[6-(methyloxy)-3-pyridazinyl]benzenesulfonamide

Produkt 1

HCID 721942794-((3,5-dimethylisoxazol-4-yl)-methoxy)-N-isobutyl-N-(6-methoxypyridazin-3-yl)benzenesulfonamideAusbeute 5,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887
Methanol
Lösungsmittel
HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

To a solution of 4-{[(3,5-dimethyl-4-isoxazolyl)methyl]oxy}-N-[6-(methyloxy)-3-pyridazinyl]benzenesulfonamide (16 mg, 0.041 mmol) in acetonitrile (1 mL) stirred at room temperature was added N″-(1,1-dimethylethyl)-N,N,N′,N′-tetramethylguanidine (7.02 mg, 0.041 mmol). The reaction mixture was stirred at 20° C. for 1 hour, then 1-bromo-2-methylpropane (8.91 μL, 0.082 mmol) was added. The reaction was heated by microwaves to 150° C. for 15 minutes. After cooling, the reaction mixture was diluted with methanol and passed through an aminopropyl (NH2) solid phase extraction (SPE) cartridge followed by a sulphonic acid (SCX) SPE cartridge, eluting with methanol. The appropriate fractions were combined and evaporated under a stream of nitrogen to give the crude product. The crude was purified by mass directed autoprep (formic acid modifier), to provide the title compound (1.0 mg). LCMS (2 min, formic) Rt 1.27 min, m/z (ES+) 447 (M+H).

Aufarbeitung

  1. temperatureThe reaction was heated by microwaves to 150° C. for 15 minutes
  2. temperatureAfter cooling
  3. extractionpassed through an aminopropyl (NH2) solid phase extraction (SPE) cartridge
  4. washeluting with methanol
  5. customevaporated under a stream of nitrogen
  6. customto give the crude product
  7. customThe crude was purified by mass

Quellen und Nachweise

ORD-Eintrag
ord-25bae4f152ea428daa2e54b793570bd5
Quelldatensatz
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09242972B2

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