Sodium Iodide → 4-[(4-Chloro-5-methoxy-2-methylphenyl)amino]-7-methoxy-8-[2-(4-methylpiperazin-1-yl)ethoxy]benzo[g]quinoline-3-carbonitrile

HRID 2213809

Reaktionsgleichung

Reaktionsgleichung von HRID 2213809
Cl[C:2]1C(OC)=CC(NC2C3C(=CC4C=C(OCCCl)C(OC)=CC=4C=3)N=CC=2C#N)=C(C)C=1.[Cl:34][C:35]1[C:63]([O:64][CH3:65])=[CH:62][C:38]([NH:39][C:40]2[C:49]3[C:44](=[CH:45][C:46]4[CH:53]=[C:52]([O:54][CH3:55])[C:51]([O:56][CH2:57]CCl)=[CH:50][C:47]=4[CH:48]=3)[N:43]=[CH:42][C:41]=2[C:60]#[N:61])=[C:37]([CH3:66])[CH:36]=1.[CH3:67][N:68]1[CH2:73][CH2:72][NH:71][CH2:70][CH2:69]1.[I-].[Na+]>COCCOC>[Cl:34][C:35]1[C:63]([O:64][CH3:65])=[CH:62][C:38]([NH:39][C:40]2[C:49]3[C:44](=[CH:45][C:46]4[CH:53]=[C:52]([O:54][CH2:55][CH2:67][N:68]5[CH2:73][CH2:72][N:71]([CH3:2])[CH2:70][CH2:69]5)[C:51]([O:56][CH3:57])=[CH:50][C:47]=4[CH:48]=3)[N:43]=[CH:42][C:41]=2[C:60]#[N:61])=[C:37]([CH3:66])[CH:36]=1

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 531671-MethylpiperazineHCID 115113674-(4-Chloro-5-methoxy-2-methylanilino)-7-methoxy-8-(chloroethoxy)benzo[g]quinoline-3-carbonitrileHCID 116702254-(4-Chloro-5-methoxy-2-methylanilino)-8-methoxy-7-(chloroethoxy)benzo[g]quinoline-3-carbonitrile

Produkt 1

HCID 53304364-[(4-Chloro-5-methoxy-2-methylphenyl)amino]-7-methoxy-8-[2-(4-methylpiperazin-1-yl)ethoxy]benzo[g]quinoline-3-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 205 mg (0.425 mmol) of 4-(4-chloro-5-methoxy-2-methylanilino)-7-methoxy-8-(chloroethoxy)benzo[g]quinoline-3-carbonitrile and 4-(4-chloro-5-methoxy-2-methylanilino)-8-methoxy-7-(chloroethoxy)benzo[g]quinoline-3-carbonitrile (1:1 mixture), 0.15 mL (1.35 mmol) of 1-methyl piperazine and 0.05 g of sodium iodide in 5 mL of ethylene glycol dimethyl ether is heated at 90° C. for 4 days under nitrogen. The mixture is cooled, the solvent is removed in vacuo and the resulting residue is stirred with saturated solution of sodium bicarbonate. The crude solid is collected by filtration, washed with water, and dried in vacuo. Purification is carried out by silica gel chromatography, eluting with a gradient of 92:8 to 85:15 methylene chloride/methanol to yield 0.10 g of 4-(4-chloro-5-methoxy-2-methylamino)-8-methoxy-7-[2-(4-methyl-1-piperazinyl)ethoxy]benzo[g]quinoline-3-carbonitrile as a yellow solid, mp 121–135° C. and 0.068 g of 4-(4-chloro-5-methoxy-2-methylanilino)-7-methoxy-8-[2-(4-methyl-1-piperazinyl)ethoxy]benzo-[g]quinoline-3-carbonitrile as a yellow solid, mp 122–137° C.

Aufarbeitung

  1. temperatureThe mixture is cooled
  2. customthe solvent is removed in vacuo
  3. filtrationThe crude solid is collected by filtration
  4. washwashed with water
  5. customdried in vacuo
  6. customPurification
  7. washeluting with a gradient of 92:8 to 85:15 methylene chloride/methanol

Quellen und Nachweise

ORD-Eintrag
ord-d534d2972faf4fb99db7e80e0187074e
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07105531B2

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