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Hydrochloric Acid → HCID 86690319, Verbindung

HRID 1521898
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1521898
Br[C:2]1[C:10]2[C:5](=[N:6][C:7]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=3)=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=3)[N:9]=2)[N:4]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([O:33]CC)=[O:32])[CH:3]=1.N#N.[Na].Cl.[CH3:40][OH:41]>O>[CH3:40][O:41][C:3]1[N:4]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32])[C:5]2=[N:6][C:7]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=3)=[C:8]([C:11]3[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][CH:16]=3)[N:9]=[C:10]2[CH:2]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 947NitrogenHCID 5360545SodiumHCID 86690318HCID 86690318, Verbindung

Produkt 1

HCID 86690319HCID 86690319, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel

Versuchsvorschrift

A mixture comprising ethyl 7-(7-bromo-2,3-di-p-tolyl-5H-pyrrolo[2,3-b]pyrazin-5-yl)heptanoate (step 1)(50 mg, 0.094 mmol) in anhydrous MeOH (1 ml) was degassed with N2 and treated with sodium (10.75 mg, 0.468 mmol). After stirring at room temperature for 30 minutes, the mixture was heated to 120° C. using microwave radiation for 1 hour. The mixture was diluted with water (20 ml) and the pH was adjusted to pH1 using 2M HCl. The aqueous was extracted with DCM (×3) and the combined organic extracts were concentrated under reduced pressure. Purification of the crude product by chromatography on silica elutuing with 0-100% EtOAc in iso-hexane followed by 10% MeOH in EtOAc afforded the titled compound as an orange solid;

Aufarbeitung

  1. temperaturethe mixture was heated to 120° C.
  2. customfor 1 hour
  3. extractionThe aqueous was extracted with DCM (×3)
  4. concentrationthe combined organic extracts were concentrated under reduced pressure
  5. customPurification of the crude product by chromatography on silica elutuing with 0-100% EtOAc in iso-hexane

Quellen und Nachweise

ORD-Eintrag
ord-e4b1e811df264a5dab65de82d981cb8a
Quelldatensatz
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09073932B2

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