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 428428Notes

Reaction equation

HRID 428428 reaction equation
[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

Participants

3

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

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.).

Workup

  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

Sources & evidence

ORD record
ord-0249b538aa7f48d5834f0a5ed4f954b6
Source dataset
uspto-grants-2001_11
Patent number
US06313290B1

Reaction notes

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