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Sodium Carbonate → (7S,8aS)-7-(4-Fluorophenoxy)methyl-2-(6-chloropyridazin-3-yl)-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazine

HRID 1594583
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1594583
[F:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][CH2:7][CH:8]2[CH2:16][N:11]3[CH2:12][CH2:13][NH:14][CH2:15][CH:10]3[CH2:9]2)=[CH:4][CH:3]=1.[Cl:19][C:20]1[N:21]=[N:22][C:23](Cl)=[CH:24][CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)CC(C)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][C@@H:8]2[CH2:16][N:11]3[CH2:12][CH2:13][N:14]([C:23]4[N:22]=[N:21][C:20]([Cl:19])=[CH:25][CH:24]=4)[CH2:15][C@@H:10]3[CH2:9]2)=[CH:17][CH:18]=1
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Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 673313,6-DichloropyridazineHCID 20682345(7RS,8aSR)-7-(4-fluorophenoxy)methyl-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazine

Produkt 1

HCID 86752025(7S,8aS)-7-(4-Fluorophenoxy)methyl-2-(6-chloropyridazin-3-yl)-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazineAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31260
Isoamyl Alcohol
Lösungsmittel

Versuchsvorschrift

A mixture of 0.500 g (2.00 mmol) of (7SR,8aSR)-7-(4-fluorophenoxy)methyl-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazine (Preparation 3), 1.49 g (10.0 mmol) of 3,6-dichloropyridazine, and 0.508 g (4.79 mmol) of sodium carbonate in 50 mL of isoamyl alcohol was heated to reflux for 48 hours. The reaction was cooled to ambient temperature, the solvent removed in vacuo, the residue taken up in ethyl acetate and water, the pH was adjusted to 11 with sodium carbonate and the layers were separated. The aqueous phase was extracted with ethyl acetate, and the combined organic layers were dried (magnesium sulfate), filtered and evaporated. Purification by flash silica gel chromatography with 90:10 ethyl acetate:hexane gave 0.478 g (66%) of the title compound. Mp (.HCl) 229° C. (dec). HRMS calc'd for C18H21ClFN4O (MH+): 363.1388, found: 363.1404.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 48 hours
  3. customthe solvent removed in vacuo
  4. customthe layers were separated
  5. extractionThe aqueous phase was extracted with ethyl acetate
  6. dry with materialthe combined organic layers were dried (magnesium sulfate)
  7. filtrationfiltered
  8. customevaporated
  9. customPurification by flash silica gel chromatography with 90:10 ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-5b553b9d9a2142fea0a99334ddd74dc2
Quelldatensatz
uspto-grants-2001_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06284757B1

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