7-Chloro-3-(aminocarbonyl)pyrazolo[3,4-c][1]benzazepine-4,10(1H,9H)-dione → 7-Chloro-3-cyanopyrazolo[3,4-c][1]benzazepine-4,10(1H,9H)-dione

HRID 428428Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 428428
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[C:6](=[O:18])[C:7]3[C:14]([C:15]([NH2:17])=O)=[N:13][NH:12][C:8]=3[C:9](=[O:11])[NH:10][C:4]=2[CH:3]=1>P(Cl)(Cl)(Cl)=O>[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[C:6](=[O:18])[C:7]3[C:14]([C:15]#[N:17])=[N:13][NH:12][C:8]=3[C:9](=[O:11])[NH:10][C:4]=2[CH:3]=1

Komponenten

3

Edukt 1

HCID 183588967-Chloro-3-(aminocarbonyl)pyrazolo[3,4-c][1]benzazepine-4,10(1H,9H)-dione2×

Produkt 1

HCID 183588857-Chloro-3-cyanopyrazolo[3,4-c][1]benzazepine-4,10(1H,9H)-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24813Phosphorus oxychlorideLösungsmittel

Versuchsvorschrift

A solution of 7-chloro-3-(aminocarbonyl)pyrazolo[3,4-c][1]benzazepine-4,10(1H,9H)-dione (590 mg, 2.03 mmol) (compound of Example 14) in phosphorous oxychloride (2.56 mL) was refluxed for 70 minutes. The excess phosphorous oxychloride was distilled off at atmospheric pressure and 106° C. To the remaining dark brown residue was added water (40 mL). The aqueous phase was extracted with ethyl acetate (4×50 mL). The organic layers were combined and dried over magnesium sulfate, filtered, and concentrated on a rotary evaporator to give the title compound as a brown/gold solid (≈216 mg, 39% yield, m.p. 370° C. dec.).

Aufarbeitung

  1. distillationThe excess phosphorous oxychloride was distilled off at atmospheric pressure and 106° C
  2. additionTo the remaining dark brown residue was added water (40 mL)
  3. extractionThe aqueous phase was extracted with ethyl acetate (4×50 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated on a rotary evaporator

Quellen und Nachweise

ORD-Eintrag
ord-0249b538aa7f48d5834f0a5ed4f954b6
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06313290B1

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