Potassium Carbonate → 2-(methoxymethyl)-1-propyl-8-[3-(4-pyridin-2-ylpiperazin-1-yl)propoxy]-1H-imidazo[4,5-c]quinolin-4-amine

HRID 540962Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 540962
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]2[N:12]=[C:11]([NH2:16])[C:10]3[N:17]=[C:18]([CH2:23][O:24][CH3:25])[N:19]([CH2:20][CH2:21][CH3:22])[C:9]=3[C:8]=2[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[N:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[N:38]1[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1>CN(C=O)C>[CH3:25][O:24][CH2:23][C:18]1[N:19]([CH2:20][CH2:21][CH3:22])[C:9]2[C:8]3[CH:7]=[C:6]([O:5][CH2:4][CH2:3][CH2:2][N:41]4[CH2:42][CH2:43][N:38]([C:33]5[CH:34]=[CH:35][CH:36]=[CH:37][N:32]=5)[CH2:39][CH2:40]4)[CH:15]=[CH:14][C:13]=3[N:12]=[C:11]([NH2:16])[C:10]=2[N:17]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 944591-(2-Pyridyl)piperazineHCID 689690038-(3-chloropropoxy)-2-methoxymethyl-1-propyl-1H-imidazo[4,5-c]quinolin-4-amine

Produkt 1

HCID 588337172-(methoxymethyl)-1-propyl-8-[3-(4-pyridin-2-ylpiperazin-1-yl)propoxy]-1H-imidazo[4,5-c]quinolin-4-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 8-(3-chloropropoxy)-2-(methoxymethyl)-1-propyl-1H-imidazo[4,5-c]quinolin-4-amine (0.20 g, 0.55 mmol, 1 equivalent), potassium carbonate (4 equivalents), and 1-(2-pyridyl)piperazine (1.1 equivalents) in DMF (5 mL) was heated at 70° C. overnight. The reaction mixture was allowed to cool to room temperature and was poured onto ice (50 g). After the mixture was stirred for 3 hours, a brown solid was isolated by filtration. The crude product was purified by chromatography on a HORIZON HPFC system (silica gel, gradient elution with 0-30% CMA in chloroform), followed by recrystallization from acetonitrile to afford 0.065 g of 2-(methoxymethyl)-1-propyl-8-[3-(4-pyridin-2-ylpiperazin-1-yl)propoxy]-1H-imidazo[4,5-c]quinolin-4-amine as off white crystals, mp 196-197° C.

Aufarbeitung

  1. temperatureto cool to room temperature
  2. additionwas poured onto ice (50 g)
  3. customa brown solid was isolated by filtration
  4. customThe crude product was purified by chromatography on a HORIZON HPFC system (silica gel, gradient elution with 0-30% CMA in chloroform)
  5. customfollowed by recrystallization from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-374e540cf8f94cf49f12b1e9bd555a98
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871782B2

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