7-(((5-Bromo-4-chloro-2-nitrophenyl)amino)methyl)-3-neopentyl-1-oxa-3-azaspiro[4.5]decan-2-one → 2-Chloro-5-(((3-neopentyl-2-oxo-1-oxa-3-azaspiro[4.5]decan-7-yl)methyl)amino)-4-nitrobenzonitrile

HRID 1423847Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1423847
Br[C:2]1[C:3]([Cl:29])=[CH:4][C:5]([N+:26]([O-:28])=[O:27])=[C:6]([NH:8][CH2:9][CH:10]2[CH2:25][CH2:24][CH2:23][C:12]3([O:16][C:15](=[O:17])[N:14]([CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:13]3)[CH2:11]2)[CH:7]=1.[Cu][C:31]#[N:32]>CN(C=O)C.[Cl-].[Na+].O>[Cl:29][C:3]1[CH:4]=[C:5]([N+:26]([O-:28])=[O:27])[C:6]([NH:8][CH2:9][CH:10]2[CH2:25][CH2:24][CH2:23][C:12]3([O:16][C:15](=[O:17])[N:14]([CH2:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:13]3)[CH2:11]2)=[CH:7][C:2]=1[C:31]#[N:32]

Komponenten

5

Edukt 2

HCID 711160457-(((5-Bromo-4-chloro-2-nitrophenyl)amino)methyl)-3-neopentyl-1-oxa-3-azaspiro[4.5]decan-2-oneHCID 178418546HCID 178418546, Verbindung

Produkt 1

HCID 711161382-Chloro-5-(((3-neopentyl-2-oxo-1-oxa-3-azaspiro[4.5]decan-7-yl)methyl)amino)-4-nitrobenzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

A suspension containing 7-(((5-bromo-4-chloro-2-nitrophenyl)amino)methyl)-3-neopentyl-1-oxa-3-azaspiro[4.5]decan-2-one (0.260 g, 0.532 mmol) and copper (I) cyanide (0.333 g, 3.72 mmol) in DMF (2 mL) was subject to microwave heating at 180° C. for 1.5 h. The reaction was cooled to rt, diluted with brine solution, and stirred for 20 min. The mixture was filtered through a pad of celite, and the celite was washed with EtOAc. The combined filtrates were washed with EtOAc. The combined organics were washed with water, dried over magnesium sulfate, filtered, and concentrated. The crude product was purified on a 24 g silica gel column (0-75% EtOAc/hexanes, 15 min gradient; 75% EtOAc/hexanes, 10 min; 35 mL/min elution; 254 nm detection) to afford the title compound as an orange solid. MS (m/z) 435.2 (M+H+).

Aufarbeitung

  1. temperatureThe reaction was cooled to rt
  2. filtrationThe mixture was filtered through a pad of celite
  3. washthe celite was washed with EtOAc
  4. washThe combined filtrates were washed with EtOAc
  5. washThe combined organics were washed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified on a 24 g silica gel column (0-75% EtOAc/hexanes, 15 min gradient; 75% EtOAc/hexanes, 10 min; 35 mL/min elution; 254 nm detection)

Quellen und Nachweise

ORD-Eintrag
ord-62dc08d999834c6d86c8806246c87833
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927585B2

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