Sodium Bicarbonate → HCID 67156805, Verbindung

HRID 221606

Reaktionsgleichung

Reaktionsgleichung von HRID 221606
[Si:1]([O:8][CH2:9][C@@H:10]([NH:26][C:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[N:30]=[CH:29][C:28]=1[NH2:37])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])=[CH:14][CH:13]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Cl.[Cl:39][CH2:40][C:41](=N)OCC.C([O-])(O)=O.[Na+]>ClCCCl>[Si:1]([O:8][CH2:9][C@@H:10]([N:26]1[C:27]2[C:36]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[N:30]=[CH:29][C:28]=2[N:37]=[C:41]1[CH2:40][Cl:39])[CH2:11][C:12]1[CH:13]=[CH:14][C:15]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])=[CH:16][CH:17]=1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 12470659Ethyl 2-chloroethanecarboximidate hydrochlorideHCID 86624132HCID 86624132, Verbindung

Produkt 1

HCID 67156805HCID 67156805, VerbindungAusbeute 81,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

N4-[(1S)-2-{[tert-Butyl(dimethyl)silyl]oxy}-1-(4-{[tert-butyl(dimethyl)silyl]oxy}benzyl)ethyl]quinoline-3,4-diamine (23.46 g, 43.6 mmol) was dissolved in 400 mL of dry 1,2-dichloroethane and the yellow solution was stirred under N2. Ethyl 2-chloroethanimidoate hydrochloride (13.8 g, 87.2 mmol) was then added and the reaction mixture was heated to 70° C. overnight. The reaction mixture was then cooled and treated with 300 mL of saturated NaHCO3 solution. The layers were separated and the organic portion was washed sequentially with saturated NaHCO3 solution and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. Chromatography (SiO2, 10-60% ethyl acetate/hexanes) gave 1-[(1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-(4-{[tert-butyl(dimethyl)silyl]oxy}benzyl)ethyl]-2-(chloromethyl)-1H-imidazo[4,5-c]quinoline (21.11 g) as a brown foam.

Aufarbeitung

  1. temperatureThe reaction mixture was then cooled
  2. customThe layers were separated
  3. washthe organic portion was washed sequentially with saturated NaHCO3 solution and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-93dc2d059fbb47cdba5ac263c67a0241
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207162B2

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