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

HRID 2203639Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2203639
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-e9ffa30c71a2424e8f5805c8accc7ec0
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09365567B2

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