Sodium Hydroxide → 3,4-Dihydro-1-methyl-6-[4-(trifluoro-methyl)phenyl]pyrrolo[1,2-a]pyrazine fumarate

HRID 486519Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 486519
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]([CH2:14][CH2:15][NH:16][C:17](=O)[CH3:18])[CH:11]=[CH:12][CH:13]=2)=[CH:5][CH:4]=1.P(Cl)(Cl)(Cl)=O.[OH-].[Na+].C(Cl)Cl.[OH-].[Na+].[C:34]([OH:41])(=[O:40])/[CH:35]=[CH:36]/[C:37]([OH:39])=[O:38]>C(O)C>[C:34]([OH:41])(=[O:40])/[CH:35]=[CH:36]/[C:37]([OH:39])=[O:38].[CH3:18][C:17]1[C:11]2[N:10]([C:9]([C:6]3[CH:7]=[CH:8][C:3]([C:2]([F:21])([F:20])[F:1])=[CH:4][CH:5]=3)=[CH:13][CH:12]=2)[CH2:14][CH2:15][N:16]=1

Komponenten

7

Edukt 5

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 444972Fumaric AcidHCID 19095353Acetamide,n-[2-[2-[4-(trifluoromethyl)phenyl]-1h-pyrrol-1-yl]ethyl]-HCID 23721229Sodium hydroxide methylene chloride

Produkt 1

HCID 190952933,4-Dihydro-1-methyl-6-[4-(trifluoro-methyl)phenyl]pyrrolo[1,2-a]pyrazine fumarateAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

N-[2-[2-[4-(Trifluoromethyl)phenyl]-pyrrol-1-yl]ethyl]acetamide (5.4 g) was treated with 25 ml of phosphorus oxychloride under argon and boiled for 1 hour while stirring. The reaction mixture was hydrolyzed at 0° C. with 100 ml of 2N sodium hydroxide solution and 150 ml of 28% sodium hydroxide methylene chloride (1×300 ml, 2×100 ml). The organic extracts were combined, dried with MgSO4 and freed from solvent. 2.5 g of a total of 5.0 g of crude product was dissolved in a 30-fold amount of ethanol and treated with 1.1 equivalents of a saturated solution of fumaric acid in ethanol. There was obtained 2.7 g (76%) of 3,4-dihydro-1-methyl-6-[4-(trifluoro-methyl)phenyl]pyrrolo[1,2-a]pyrazine fumarate (1:1); m.pt.: 165°-167° C. (dec.).

Aufarbeitung

  1. dry with materialdried with MgSO4
  2. dissolution2.5 g of a total of 5.0 g of crude product was dissolved in a 30-fold amount of ethanol

Quellen und Nachweise

ORD-Eintrag
ord-6f708ed2478e4258bd97b4f442812feb
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05292732

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