Hydrochloric Acid → 3-ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentanone

HRID 1969552Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1969552
[CH2:1]([C@@H:3]1[CH2:11][C:6]2(OCC[O:7]2)[CH2:5][C@@H:4]1[C:12]1[N:16]2[C:17]3[CH:23]=[CH:22][N:21]([S:24]([C:27]4[CH:33]=[CH:32][C:30]([CH3:31])=[CH:29][CH:28]=4)(=[O:26])=[O:25])[C:18]=3[N:19]=[CH:20][C:15]2=[N:14][N:13]=1)[CH3:2].Cl>C1COCC1>[CH2:1]([CH:3]1[CH:4]([C:12]2[N:16]3[C:17]4[CH:23]=[CH:22][N:21]([S:24]([C:27]5[CH:28]=[CH:29][C:30]([CH3:31])=[CH:32][CH:33]=5)(=[O:26])=[O:25])[C:18]=4[N:19]=[CH:20][C:15]3=[N:14][N:13]=2)[CH2:5][C:6](=[O:7])[CH2:11]1)[CH3:2]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 679986721-((7S,8R)-8-ethyl-1,4-dioxaspiro[4.4]nonan-7-yl)-6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine

Produkt 1

HCID 585571653-ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentanoneAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A round bottom flask was charged with 1-((7S,8R)-8-ethyl-1,4-dioxaspiro[4.4]nonan-7-yl)-6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine (3.56 g, 7.61 mmol) and THF (20 mL). To the solution was added aqueous HCl (6N, 3.81 mL, 22.8 mmol) and the mixture was stirred at rt for about 2 h. The solvent was removed under reduced pressure and DCM (75 mL) and water (50 mL) were added. The layers were separated and the organic solution was dried over anhydrous MgSO4, filtered, and concd under reduced pressure to give 3-ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentanone as a brown foam (2.99 g, 93%): LC/MS (Table 1, Method c) Rt=1.40 min; MS m/z: 424 (M+H)+.

Aufarbeitung

  1. customThe solvent was removed under reduced pressure and DCM (75 mL) and water (50 mL)
  2. additionwere added
  3. customThe layers were separated
  4. dry with materialthe organic solution was dried over anhydrous MgSO4
  5. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-a1957f0e68f9411ca09f8f2fa9a9dcc0
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08426411B2

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