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Water → HCID 58382317, Verbindung

HRID 1628026
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1628026
[Br:1][C:2]1[N:3]=[C:4]([C:24]2[C:25]([CH3:30])=[N:26][CH:27]=[CH:28][CH:29]=2)[N:5]2[C:10]3[CH:11]=[CH:12][N:13]([S:14]([C:17]4[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=4)(=[O:16])=[O:15])[C:9]=3[N:8]=[CH:7][C:6]=12.[OH2:31]>O1CCOCC1>[Br:1][C:2]1[N:3]=[C:4]([C:24]2[C:25]([CH:30]=[O:31])=[N:26][CH:27]=[CH:28][CH:29]=2)[N:5]2[C:10]3[CH:11]=[CH:12][N:13]([S:14]([C:17]4[CH:18]=[CH:19][C:20]([CH3:21])=[CH:22][CH:23]=4)(=[O:16])=[O:15])[C:9]=3[N:8]=[CH:7][C:6]=12
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 962WaterHCID 583824443-bromo-1-(2-methylpyridin-3-yl)-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine

Produkt 1

HCID 58382317HCID 58382317, VerbindungAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

The 3-bromo-1-(2-methylpyridin-3-yl)-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine (0.500 g, 1.03 mmol, prepared using J.1 from Example #2, Step B with 2-methylnicotinic acid, L.2 with POCl3 and AB) in 1,4-dioxane (20 mL) was treated with SeO2 (0.210 g, 1.89 mmol) then the mixture was heated at about 105° C. for about 1 h. The mixture was cooled to rt then water (0.6 mL) was added. The mixture was heated to reflux for about 3 days. The mixture was cooled to rt then concentrated in vacuo. The material was purified using a 10 g silica column eluting with EtOAc. The impure fractions were combined and concentrated then the material was purified using a 10 g silica column eluting with EtOAc. The materials were combined to give 3-(3-bromo-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)picolinaldehyde (0.355 g, 69%): LC/MS (Table 2, Method b) Rt=3.53 min; MS m/z 480 (M+H)+.

Aufarbeitung

  1. temperatureThe mixture was cooled to rt
  2. temperatureThe mixture was heated
  3. temperatureto reflux for about 3 days
  4. temperatureThe mixture was cooled to rt
  5. concentrationthen concentrated in vacuo
  6. customThe material was purified
  7. washeluting with EtOAc
  8. concentrationconcentrated
  9. customthe material was purified
  10. washeluting with EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-f119cdc2401d43ee80f4428235d57f59
Quelldatensatz
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08785639B2

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