4-Quinolinecarboxylic acid, 3-hydroxy-2-methyl- → [6-Methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolin-7-yl]-(2-morpholin-4-yl-ethyl)-amine

HRID 229015Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 229015
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([NH:14][CH2:15][CH2:16][N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[OH:23][C:24]1[C:25]([CH3:37])=[N:26][C:27]2[C:32]([C:33]=1C(O)=O)=[CH:31][CH:30]=[CH:29][CH:28]=2>CN(C)C1C=CN=CC=1.ClC1C=CC=CC=1Cl>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[NH:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)[N:5]=[CH:4][CH:3]=[C:2]2[O:23][C:24]1[C:25]([CH3:37])=[N:26][C:27]2[C:32]([CH:33]=1)=[CH:31][CH:30]=[CH:29][CH:28]=2

Komponenten

5

Edukt 2

HCID 670244-Quinolinecarboxylic acid, 3-hydroxy-2-methyl-HCID 23078325(4-Chloro-6-methoxy-quinolin-7-yl)-(2-morpholin-4-yl-ethyl)-amine

Produkt 1

HCID 23078376[6-Methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolin-7-yl]-(2-morpholin-4-yl-ethyl)-amineAusbeute 16,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 72391,2-DichlorobenzeneLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

(4-Chloro-6-methoxy-quinolin-7-yl)-(2-morpholin-4-yl-ethyl)-amine (53 mg), 3-hydroxy-2-methyl-quinolin-4-carboxylic acid (126 mg), and 4-dimethylaminopyridine (200 mg) were suspended in o-dichlorobenzene (8 ml). The suspension was stirred at 140° C. overnight. The reaction solution was cooled to room temperature, and the solvent was removed by distillation under the reduced pressure. Water was then added to the residue, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography using methanol-chloroform to give the title compound (12 mg, yield 16%).

Aufarbeitung

  1. temperatureThe reaction solution was cooled to room temperature
  2. customthe solvent was removed by distillation under the reduced pressure
  3. additionWater was then added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with water
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. customThe solvent was removed by distillation under the reduced pressure
  8. customthe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-60f2c0707c31485a96b9c152ab20e237
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560558B2

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