Potassium Carbonate → HCID 178454118, Verbindung

HRID 707222Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 707222
[C:1]([O:5][C:6](=[O:13])[NH:7][C@H:8]1[CH2:11][C@H:10]([NH2:12])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].Cl[C:15]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][CH:18]=[CH:17][N:16]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[C:1]([O:5][C:6](=[O:13])[NH:7][C@H:8]1[CH2:11][C@H:10]([NH:12][C:15]2[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][CH:18]=[CH:17][N:16]=2)[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 796132-Chloro-3-nitropyridineHCID 178454111HCID 178454111, Verbindung

Produkt 1

HCID 178454118HCID 178454118, VerbindungAusbeute 63,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

Tert-butyl(trans-3-aminocyclobutyl)carbamate (1.38 g, 7.41 mmol), 2-chloro-3-nitropyridine (1.25 g, 7.88 mmol) and potassium carbonate (0.655 ml, 10.85 mmol) were combined in dry dimethylsulfoxide (20 mL) and heated at 110° C. After 2 hours the reaction was cooled and partitioned between ethyl acetate (300 mL) and water (300 mL). The organic was dried with magnesium sulfate and evaporated to dryness under reduced pressure. Purification using silica chromatography (dichloromethane to ethyl acetate gradient) gave the desired tert-butyl(trans-3-((3-nitropyridin-2-yl)amino)cyclobutyl)carbamate (1.45 g, 4.70 mmol, 63.5% yield).

Aufarbeitung

  1. temperatureAfter 2 hours the reaction was cooled
  2. custompartitioned between ethyl acetate (300 mL) and water (300 mL)
  3. dry with materialThe organic was dried with magnesium sulfate
  4. customevaporated to dryness under reduced pressure
  5. customPurification

Quellen und Nachweise

ORD-Eintrag
ord-f281a7e02d4549518dc48cec6f881429
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09174992B2

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