Chloroacetyl chloride → HCID 66958446, Verbindung

HRID 598392Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 598392
C(N(CC)CC)C.[NH2:8][C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1[NH:19][CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:16][CH:15]=[C:14]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH:13]=2.[Cl:38][CH2:39][C:40](Cl)=O>ClCCl>[CH2:31]([O:30][C:14]1[CH:15]=[CH:16][C:17]2[C:18]3[N:19]([CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:40]([CH2:39][Cl:38])=[N:8][C:9]=3[CH:10]=[N:11][C:12]=2[CH:13]=1)[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Komponenten

5

Edukt 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 66958391Tert-butyl 2-[(3-amino-7-benzyloxyquinolin-4-yl)amino]ethylcarbamate

Produkt 1

HCID 66958446HCID 66958446, VerbindungAusbeute 15,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Triethylamine (24.0 mL, 172.58 mmol) was added to a solution of tert-butyl 2-[(3-amino-7-benzyloxyquinolin-4-yl)amino]ethylcarbamate (35.25 g, 86.29 mmol) in dichloromethane (400 mL) and stirred at ambient temperature. Chloroacetyl chloride (6.87 mL, 86.29 mmol) was quickly added at ambient temperature to avoid splashing and was stirred for 10 minutes. The reaction mixture was concentrated under reduced pressure, dissolved in ethanol (500 mL), and stirred for 2 days at ambient temperature. The mixture was concentrated under reduced pressure and the residue was recrystallized from dichloromethane to afford 6.23 g of tert-butyl 2-(7-benzyloxy-2-chloromethyl-1H-imidazo[4,5-c]quinolin-1-yl)ethylcarbamate.

Aufarbeitung

  1. stirringwas stirred for 10 minutes
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutiondissolved in ethanol (500 mL)
  4. stirringstirred for 2 days at ambient temperature
  5. concentrationThe mixture was concentrated under reduced pressure
  6. customthe residue was recrystallized from dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-e64f5c19a46443f3b39d661496326f46
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897597B2

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