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Hydrazine hydrate (1:1) → 1-(4-Aminopiperidino)-4-(3-chloro-4-methoxybenzyl)amino-6-cyanophthalazine dihydrochloride

HRID 2300171
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2300171
[Cl:1][C:2]1[CH:3]=[C:4]([CH:36]=[CH:37][C:38]=1[O:39][CH3:40])[CH2:5][NH:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]#[N:18])[CH:15]=2)[C:10]([N:19]2[CH2:24][CH2:23][CH:22]([N:25]3C(=O)C4=CC=CC=C4C3=O)[CH2:21][CH2:20]2)=[N:9][N:8]=1.O.NN>C(O)C>[ClH:1].[ClH:1].[NH2:25][CH:22]1[CH2:21][CH2:20][N:19]([C:10]2[C:11]3[C:16](=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=3)[C:7]([NH:6][CH2:5][C:4]3[CH:36]=[CH:37][C:38]([O:39][CH3:40])=[C:2]([Cl:1])[CH:3]=3)=[N:8][N:9]=2)[CH2:24][CH2:23]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 227445114-(3-Chloro-4-methoxybenzyl)amino-6-cyano-1-(4-phthalimidopiperidino)phthalazine

Produkt 1

HCID 227446461-(4-Aminopiperidino)-4-(3-chloro-4-methoxybenzyl)amino-6-cyanophthalazine dihydrochlorideAusbeute 30,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 4.85 g of the resulting 4-(3-chloro-4-methoxybenzyl)amino-6-cyano-1-(4-phthalimidopiperidino)phthalazine, 4 ml hydrazine monohydrate and 40 ml ethanol was heated under reflux for 1 hr. The reaction solution was evaporated, dissolved in ethyl acetate, and 1 N hydrochloric acid was added thereto to adjust the pH thereof to 3, and the insoluble matters were removed by filtration. The aqueous layer in the filtrate was adjusted to pH 11 with 1 N sodium hydroxide, and then extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, evaporated, and then purified by silica gel column chromatography. The resulting product was suspended in ethanol/water, then 1 N aqueous hydrochloric acid was added thereto and dissolved by heating. After cooling, the resulting crystals were collected by filtration to give 440 mg of the title compound as a yellow powder.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hr
  3. customThe reaction solution was evaporated
  4. dissolutiondissolved in ethyl acetate
  5. addition1 N hydrochloric acid was added
  6. customto 3, and the insoluble matters were removed by filtration
  7. extractionextracted with ethyl acetate
  8. washThe organic layer was washed with brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. customevaporated
  11. custompurified by silica gel column chromatography
  12. addition1 N aqueous hydrochloric acid was added
  13. dissolutiondissolved
  14. temperatureby heating
  15. temperatureAfter cooling
  16. filtrationthe resulting crystals were collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-e9a88284f3ae4a2887d40c5467c0e67d
Quelldatensatz
uspto-grants-2002_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06498159B1

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