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Hydrochloric Acid → N4-{4-[(3-Ethyl-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]-3-fluorophenyl}-6-(trifluoromethyl)pyrimidine-2,4-diamine

HRID 2192187
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2192187
[CH2:1]([C:3]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][C:10]=2[O:12][C:13]2[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][C:14]=2[F:20])[NH:5][CH:4]=1)[CH3:2].N1C=CC=NC=1N.Cl.Cl[C:30]1[CH:35]=[C:34]([C:36]([F:39])([F:38])[F:37])[N:33]=[C:32]([NH2:40])[N:31]=1.[OH-].[Na+]>O>[CH2:1]([C:3]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][C:10]=2[O:12][C:13]2[CH:19]=[CH:18][C:16]([NH:17][C:30]3[CH:35]=[C:34]([C:36]([F:39])([F:37])[F:38])[N:33]=[C:32]([NH2:40])[N:31]=3)=[CH:15][C:14]=2[F:20])[NH:5][CH:4]=1)[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 313Hydrochloric Acid2×HCID 79782-AminopyrimidineHCID 14798Sodium HydroxideHCID 130869074-Chloro-6-(trifluoromethyl)pyrimidin-2-amineHCID 597410004-[(3-Ethyl-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]-3-fluoroaniline

Produkt 1

HCID 11502907
N4-{4-[(3-Ethyl-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]-3-fluorophenyl}-6-(trifluoromethyl)pyrimidine-2,4-diamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

45 mg (0.17 mmol) of 4-[(3-ethyl-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]-3-fluoroaniline and 34 mg (0.17 mmol) of 4-chloro-6-trifluoromethyl)pyrimidine-2-amine are suspended in 5 ml of water. 24 μl of 37% strength hydrochloric acid are added, and the mixture is heated at reflux overnight. Another 70 mg (0.35 mmol) of 4-chloro-6-(trifluoromethyl)pyrimidine-2-amine and 40 μl of 37% strength hydrochloric acid are then added, and the mixture is heated at reflux for another night. Using 1N aqueous sodium hydroxide solution, the pH is then adjusted to 10. The mixture is concentrated under reduced pressure and the residue is purified by column chromatography on silica gel (mobile phase: dichloromethane/methanol 100:1 to 10:1). The product obtained is purified further by preparative HPLC.

Aufarbeitung

  1. temperaturethe mixture is heated
  2. temperatureat reflux overnight
  3. temperaturethe mixture is heated
  4. temperatureat reflux for another night
  5. concentrationThe mixture is concentrated under reduced pressure
  6. customthe residue is purified by column chromatography on silica gel (mobile phase: dichloromethane/methanol 100:1 to 10:1)
  7. customThe product obtained
  8. customis purified further by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-5ea1cb1abebe4314b1481cb153e23b57
Quelldatensatz
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08329716B2

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