Triethylamine → 7-bromo-2-ethoxymethyl-1-{[1-(2-methylpropylcarbonyl)piperidin-4-yl]methyl}-1H-imidazo[4,5-c]quinolin-4-amine

HRID 9511

Reaktionsgleichung

Reaktionsgleichung von HRID 9511
Cl.Cl.[Br:3][C:4]1[CH:5]=[CH:6][C:7]2[C:8]3[N:17]([CH2:18][CH:19]4[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]4)[C:16]([CH2:25][O:26][CH2:27][CH3:28])=[N:15][C:9]=3[C:10]([NH2:14])=[N:11][C:12]=2[CH:13]=1.C(N(CC)CC)C.[C:36](Cl)(=O)[CH:37]([CH3:39])[CH3:38].[C:42](OCC)(=[O:44])C>C(Cl)(Cl)Cl>[Br:3][C:4]1[CH:5]=[CH:6][C:7]2[C:8]3[N:17]([CH2:18][CH:19]4[CH2:24][CH2:23][N:22]([C:42]([CH2:36][CH:37]([CH3:39])[CH3:38])=[O:44])[CH2:21][CH2:20]4)[C:16]([CH2:25][O:26][CH2:27][CH3:28])=[N:15][C:9]=3[C:10]([NH2:14])=[N:11][C:12]=2[CH:13]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 62325Isobutyryl chlorideHCID 219844087-bromo-2-ethoxymethyl-1-(piperidin-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-4-amine dihydrochloride

Produkt 1

HCID 219842427-bromo-2-ethoxymethyl-1-{[1-(2-methylpropylcarbonyl)piperidin-4-yl]methyl}-1H-imidazo[4,5-c]quinolin-4-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A solution of 7-bromo-2-ethoxymethyl-1-(piperidin-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-4-amine dihydrochloride (4.0 g, 8.1 mmol) and triethylamine (5.67 mL, 40.7 mmol) in chloroform (300 mL) was treated with isobutyryl chloride (0.85 mL, 8.1 mmol) according to the method described in Part A of Examples 583–611. The reaction was complete after one hour. Following trituration with ethyl acetate, the solid was recrystallized from ethyl acetate and then triturated with hot acetonitrile and isolated by filtration to provide 3.63 g of 7-bromo-2-ethoxymethyl-1-{[1-(2-methylpropylcarbonyl)piperidin-4-yl]methyl}-1H-imidazo[4,5-c]quinolin-4-amine as a white solid, mp 199–200° C.

Aufarbeitung

  1. customthe solid was recrystallized from ethyl acetate
  2. customtriturated with hot acetonitrile
  3. customisolated by filtration

Quellen und Nachweise

ORD-Eintrag
ord-99bd2886c8094accacefd852ba8f9685
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091214B2

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