Hydrochloric Acid → 2-(4-{4-[(2-Aminopyrimidin-4-yl)amino]-2-fluorophenoxy}-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanol

HRID 2192190Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2192190
[NH2:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]3[NH:13][CH:14]=[C:15]([CH2:16][CH2:17][OH:18])[C:8]=23)=[C:4]([F:21])[CH:3]=1.Cl[C:23]1[CH:28]=[CH:27][N:26]=[C:25]([NH2:29])[N:24]=1.Cl.[OH-].[Na+]>O>[NH2:29][C:25]1[N:26]=[C:27]([NH:1][C:2]2[CH:20]=[CH:19][C:5]([O:6][C:7]3[CH:12]=[CH:11][N:10]=[C:9]4[NH:13][CH:14]=[C:15]([CH2:16][CH2:17][OH:18])[C:8]=34)=[C:4]([F:21])[CH:3]=2)[CH:28]=[CH:23][N:24]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2233322-Amino-4-chloropyrimidineHCID 210815442-[4-(4-Amino-2-fluorophenoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl]ethanol

Produkt 1

HCID 116250992-(4-{4-[(2-Aminopyrimidin-4-yl)amino]-2-fluorophenoxy}-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

135 mg (0.47 mmol) of 2-[4-(4-amino-2-fluorophenoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl]ethanol and 79 mg (0.61 mmol) of 4-chloropyrimidine-2-amine are suspended in 6 ml of water. 0.6 ml (0.6 mmol) of 1N hydrochloric acid is added, and the mixture is heated at reflux overnight. Using 1N aqueous sodium hydroxide solution, the suspension is adjusted to pH 10, resulting in the precipitation of crystals. The crystals are filtered off with suction, washed with water and purified by column chromatography on silica gel (mobile phase: dichloromethane/methanol (7N ammonia) 100:1 to 10:1).

Aufarbeitung

  1. temperaturethe mixture is heated
  2. temperatureat reflux overnight
  3. customresulting in the precipitation of crystals
  4. filtrationThe crystals are filtered off with suction
  5. washwashed with water
  6. custompurified by column chromatography on silica gel (mobile phase: dichloromethane/methanol (7N ammonia) 100:1 to 10:1)

Quellen und Nachweise

ORD-Eintrag
ord-ab288ecfa6fc4cea9efb44e887cacaa9
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08329716B2

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