2-Hydrazinyl-N,N-dimethylethanamine → 5-chloro-2-[2-(dimethylamino)ethyl]-10-(p-methoxybenzyloxy) isoquino[5,6,7-cd]indazole-6(2H)-one

HRID 234827

Reaktionsgleichung

Reaktionsgleichung von HRID 234827
[CH3:1][N:2]([CH3:7])[CH2:3][CH2:4][NH:5][NH2:6].[Cl:8][C:9]1[C:22]2[C:21](=[O:23])[C:20]3[CH:19]=[N:18][CH:17]=[C:16]([O:24][CH2:25][C:26]4[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=4)[C:15]=3[C:14](=O)[C:13]=2[C:12](F)=[CH:11][CH:10]=1>N1C=CC=CC=1>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]2[N:5]([CH2:4][CH2:3][N:2]([CH3:7])[CH3:1])[N:6]=[C:14]3[C:15]4[C:16]([O:24][CH2:25][C:26]5[CH:27]=[CH:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=5)=[CH:17][N:18]=[CH:19][C:20]=4[C:21](=[O:23])[C:22]=1[C:13]=23

Komponenten

4

Edukt 2

HCID 1205522-Hydrazinyl-N,N-dimethylethanamineHCID 153619409-Chloro-6-fluoro-4-(p-methoxy benzyloxy)benzo[g]isoquinoline-5,10-dione

Produkt 1

HCID 106477695-chloro-2-[2-(dimethylamino)ethyl]-10-(p-methoxybenzyloxy) isoquino[5,6,7-cd]indazole-6(2H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A solution of N-[2-(dimethylamino)ethyl]hydrazine (8.5 mg) in pyridine (0.5 mL) is added to 9-chloro-6-fluoro-4-(p-methoxybenzyloxy) benzo[g]isoquinoline-5,10-dione of Preparative Example 29 (13 mg) over a period of 2 minutes at 0° C. under a nitrogen blanket and the mixture is stirred for 2 h. The excess pyridine and some excess hydrazine are removed under a nitrogen stream. The residue is placed under vacuum overnight. The product is purified by thick layer chromathography (silica gel, 10 cm by 20 cm) using 4% methanol/96% dicloromethane. The major yellow band is scraped from the plate and the yellow compound extracted into 25% methanol/75% dicloromethane. Removal of the solvent gives 5-chloro-2-[2-(dimethylamino)ethyl]-10-(p-methoxybenzyloxy) isoquino[5,6,7-cd]indazole-6(2H)-one (3 mg) as an amorphous solid.

Aufarbeitung

  1. customThe excess pyridine and some excess hydrazine are removed under a nitrogen stream
  2. customis placed under vacuum overnight
  3. customThe product is purified by thick layer chromathography (silica gel, 10 cm by 20 cm)
  4. extractionthe yellow compound extracted into 25% methanol/75% dicloromethane
  5. customRemoval of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-32bfe993475a41df8acf5a5c914ae87b
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05596097

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