Ammonium Hydroxide → 2-ethoxymethyl-7-phenyl-1-(piperidin-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-4-amine

HRID 1818150Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1818150
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:29][O:30][CH2:31][CH3:32])[N:14]([CH2:15][CH:16]3[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]3)[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:5][C:4]=2[N:3]=1.[OH-].[NH4+]>O>[CH2:31]([O:30][CH2:29][C:13]1[N:14]([CH2:15][CH:16]2[CH2:17][CH2:18][NH:19][CH2:20][CH2:21]2)[C:10]2[C:9]3[CH:8]=[CH:7][C:6]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[CH:5][C:4]=3[N:3]=[C:2]([NH2:1])[C:11]=2[N:12]=1)[CH3:32]

Komponenten

4

Edukt 2

HCID 14923Ammonium HydroxideHCID 21984025tert-Butyl 4-[(4-amino-2-ethoxymethyl-7-phenyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]piperidine-1-carboxylate

Produkt 1

HCID 100474812-ethoxymethyl-7-phenyl-1-(piperidin-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-4-amineAusbeute 54,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

tert-Butyl 4-[(4-amino-2-ethoxymethyl-7-phenyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]piperidine-1-carboxylate (0.64 g) was deprotected according to the method described in Example 177. The crude solid was dissolved in water (10 mL), and ammonium hydroxide was added until the solution was basic. The mixture was then extracted with chloroform (2×10 mL), and the combined extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was recrystallized from acetonitrile and dried for 16 hours in a vacuum oven at 60° C. to provide 0.28 g of 2-ethoxymethyl-7-phenyl-1-(piperidin-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-4-amine as a white, crystalline solid, mp 142-143° C.

Aufarbeitung

  1. extractionThe mixture was then extracted with chloroform (2×10 mL)
  2. dry with materialthe combined extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from acetonitrile
  6. customdried for 16 hours in a vacuum oven at 60° C.

Quellen und Nachweise

ORD-Eintrag
ord-b504bfc7fde143b1a550d952fdce05ac
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07598382B2

Notizen zur Reaktion

Wird geladen…