Hydrazine → 2-[2-(N-tert-butoxycarbonylamino)ethyl]-5-(p-toluenesulfonyl oxy)isoquino[8,7,6cd]indazole-6(2H)-one

HRID 440361

Reaktionsgleichung

Reaktionsgleichung von HRID 440361
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10]Cl)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:12][NH2:13].F[C:15]1[C:28]2[C:27](=O)[C:26]3[CH:25]=[N:24][CH:23]=[CH:22][C:21]=3[C:20](=[O:30])[C:19]=2[C:18]([O:31][S:32]([C:35]2[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=2)(=[O:34])=[O:33])=[CH:17][CH:16]=1.ClC1C2C(=O)C3C=NC=CC=3C(=O)C=2C(OS(C2C=CC(C)=CC=2)(=O)=O)=CC=1.C(N(CC)C(C)C)(C)C>C1COCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][N:12]1[C:15]2[CH:16]=[CH:17][C:18]([O:31][S:32]([C:35]3[CH:36]=[CH:37][C:38]([CH3:41])=[CH:39][CH:40]=3)(=[O:33])=[O:34])=[C:19]3[C:20](=[O:30])[C:21]4[CH:22]=[CH:23][N:24]=[CH:25][C:26]=4[C:27]([C:28]=23)=[N:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

7

Edukt 5

HCID 9321HydrazineHCID 81531DiisopropylethylamineHCID 3795708N-Boc-2-chloroethylamineHCID 105728809-Fluoro-6-(p-toluenesulfonyloxy)benzo[g]isoquinoline-5,10-dioneHCID 199747549-Chloro-6-(p-toluenesulfonyloxy)benzo[g]isoquinoline-5,10-dione

Produkt 1

HCID 105064812-[2-(N-tert-butoxycarbonylamino)ethyl]-5-(p-toluenesulfonyl oxy)isoquino[8,7,6cd]indazole-6(2H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

(2-N-tert-butoxycarbonylaminoethyl)hydrazine is prepared by reaction of N-t-butoxycarbonyl-2-chloroethylamine with hydrazine following a procedure adapted from J. Med. Chem. 7, 493, (1964). Under a nitrogen atmosphere a solution of (2-N-tert-butoxycarbonylaminoethyl)hydrazine (9.2 g) in anhydrous THF (10 mL) is added during 30' to the stirred 9:1 mixture of 9-fluoro-6-(p-toluenesulfonyloxy)benzo[g]isoquinoline-5,10-dione and 9-chloro-6-(p-toluenesulfonyloxy)benzo [g]isoquinoline-5,10-dione of Preparative Example 10b (3.0 g) in THF (25 mL) containing N,N-diisopropylethylamine (1.38 mL). A slightly exothermic reaction ensues, and the reaction temperature increases from 21° C. to 24° C. After stirring for one hour at room temperature the obtained precipitate is recovered by suction, washed with THF/n-hexane 1/1 (15 mL) and dried at 40° C. under vacuum, to give 2-[2-(N-tert-butoxycarbonylamino)ethyl]-5-(p-toluenesulfonyloxy)isoquino[8,7,6-cd]indazole-6(2H)-one (1.33 g).

Aufarbeitung

  1. customA slightly exothermic reaction
  2. temperaturethe reaction temperature increases from 21° C. to 24° C
  3. stirringAfter stirring for one hour at room temperature the obtained precipitate
  4. customis recovered by suction
  5. washwashed with THF/n-hexane 1/1 (15 mL)
  6. customdried at 40° C. under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-fddde0695d034db8b269b8ef50e7c34c
Quelldatensatz
uspto-grants-1996_05
Patentnummer
US05519029

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