Sodium hydride → 5-Cyclopentyloxy-1-(3,5-dichloropyridin-4-ylmethyl)-6-methoxy-phthalazine

HRID 1250853

Reaktionsgleichung

Reaktionsgleichung von HRID 1250853
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[N:6][CH:7]=[C:8]([Cl:11])[C:9]=1[CH3:10].Cl[C:13]1[C:22]2[C:17](=[C:18]([O:25][CH:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)[C:19]([O:23][CH3:24])=[CH:20][CH:21]=2)[CH:16]=[N:15][N:14]=1>CN(C=O)C>[Cl:3][C:4]1[CH:5]=[N:6][CH:7]=[C:8]([Cl:11])[C:9]=1[CH2:10][C:13]1[C:22]2[C:17](=[C:18]([O:25][CH:26]3[CH2:27][CH2:28][CH2:29][CH2:30]3)[C:19]([O:23][CH3:24])=[CH:20][CH:21]=2)[CH:16]=[N:15][N:14]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 109538273,5-Dichloro-4-methylpyridineHCID 118219611-Chloro-5-cyclopentyloxy-6-methoxy-phthalazine

Produkt 1

HCID 98659165-Cyclopentyloxy-1-(3,5-dichloropyridin-4-ylmethyl)-6-methoxy-phthalazineAusbeute 57,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

Under stirring, 55% sodium hydride (3.73 g, 85.56 mmoles) was added to a solution, under nitrogen, of 3,5-dichloro-4-methyl-pyridine (13.86 g, 85.56 mmoles) in anhydrous DMF (100 ml). The mixture was kept under stirring for 1 hour then added with a solution of 1-chloro-5-cyclopentyloxy-6-methoxy-phthalazine (7.95 g, 28.52 mmoles), obtained as described in example 7, in anhydrous dimethylformamide (70 ml). After resting overnight, the mixture was quenched with water, diluted with water and extracted with ethyl acetate. The extract was washed with water and dried on sodium sulphate, then evaporated to dryness. The residue was flash chromatographed (eluent petrolatum/ethyl acetate 1:1) to give 6.58 g of the title compound (yield: 57%).

Aufarbeitung

  1. stirringunder stirring for 1 hour
  2. customobtained
  3. customthe mixture was quenched with water
  4. additiondiluted with water
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water
  7. customdried on sodium sulphate
  8. customevaporated to dryness
  9. customchromatographed (eluent petrolatum/ethyl acetate 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-00569ee8d4b944d9b7cff0b9d89c3f73
Quelldatensatz
uspto-grants-2002_01
Patentnummer
US06340684B1

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