Ethyl 2-chloroethanecarboximidate hydrochloride → HCID 86624123, Verbindung

HRID 221559

Reaktionsgleichung

Reaktionsgleichung von HRID 221559
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][C@@H:13]([CH3:23])[CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:9][CH:8]=[CH:7][CH:6]=2.Cl.[Cl:25][CH2:26][C:27](=N)OCC>ClCCCl>[Cl:25][CH2:26][C:27]1[N:12]([C@@H:13]([CH3:23])[CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:21])[CH3:20])[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=1

Komponenten

4

Edukt 2

HCID 12470659Ethyl 2-chloroethanecarboximidate hydrochlorideHCID 86624121HCID 86624121, Verbindung

Produkt 1

HCID 86624123HCID 86624123, VerbindungAusbeute 46,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

tert-Butyl (2S)-2-[(3-aminoquinolin-4-yl)amino]propylcarbamate (4.60 g, 14.55 mmol) was dissolved in 150 mL of anhydrous 1,2-dichloroethane and the solution was stirred under N2. Ethyl 2-chloroethanimidoate hydrochloride (3.45 g, 21.8 mmol) was added and the reaction was heated to 60° C. for 24 hours. The reaction mixture was cooled and washed with saturated sodium bicarbonate solution (2×100 mL) followed by brine. The organic layer was dried over Na2SO4, filtered, and concentrated to give an orange solid. Chromatography (SiO2, 60-80% EtOAc/hexanes) gave tert-butyl (2S)-2-[2-(chloromethyl)-1H-imidazo[4,5-c]quinolin-1-yl]propylcarbamate (2.54 g) as a tan solid.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. washwashed with saturated sodium bicarbonate solution (2×100 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give an orange solid

Quellen und Nachweise

ORD-Eintrag
ord-5181d69792a14636827cd7006264b6b2
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207162B2

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