Methanol → 2-(4-Fluorobenzyl)-10-hydroxy-4-(hydroxymethyl)-8-methyl-7,8-dihydropyrazino[1',2':1,5]pyrrolo[2,3-d]pyridazine-1,9(2H,6H)-dione

HRID 494126Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 494126
[F:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11]3[C:14]([O:23]C)=[C:15]4[C:20](=[O:21])[N:19]([CH3:22])[CH2:18][CH2:17][N:16]4[C:10]=3[C:9]([CH2:25][OH:26])=[N:8]2)=[CH:4][CH:3]=1.B(Br)(Br)Br.CO>ClCCl>[F:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11]3[C:14]([OH:23])=[C:15]4[C:20](=[O:21])[N:19]([CH3:22])[CH2:18][CH2:17][N:16]4[C:10]=3[C:9]([CH2:25][OH:26])=[N:8]2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 25134Boron tribromideHCID 688646802-(4-fluorobenzyl)-4-(hydroxymethyl)-10-methoxy-8-methyl-7,8-dihydropyrazino[1',2':1,5]pyrrolo[2,3-d]pyridazine-1,9(2H,6H)-dione

Produkt 1

HCID 547043072-(4-Fluorobenzyl)-10-hydroxy-4-(hydroxymethyl)-8-methyl-7,8-dihydropyrazino[1',2':1,5]pyrrolo[2,3-d]pyridazine-1,9(2H,6H)-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 2-(4-fluorobenzyl)-4-(hydroxymethyl)-10-methoxy-8-methyl-7,8-dihydropyrazino[1′,2′:1,5]pyrrolo[2,3-d]pyridazine-1,9(2H,6H)-dione (27 mg g, 70 μmol) in anhydrous dichloromethane (1 mL), a solution of boron tribromide in dichloromethane (90 μL, 90 μmol; 1 M) was added. After stirring at room temperature for one hour, the reaction mixture was treated with anhydrous methanol (2 mL), stirred for 30 minutes, and concentrated under vacuum. The procedure was repeated twice. The residue was subjected to purification on preparative reverse phase high pressure column chromatography. Collection and lyophilization of appropriate fractions provided the title compound.

Aufarbeitung

  1. stirringstirred for 30 minutes
  2. concentrationconcentrated under vacuum
  3. customThe residue was subjected to purification on preparative reverse phase high pressure column chromatography
  4. customCollection and lyophilization of appropriate fractions

Quellen und Nachweise

ORD-Eintrag
ord-7b3ef64c7ffc4ed6ac30cf37c806860b
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07538112B2

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