Maleic Anhydride → HCID 54170922, Verbindung

HRID 1698937Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1698937
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Br:19])[CH:14]=3)=[N:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[C:20]1(=[O:26])[O:25][C:23](=[O:24])[CH:22]=[CH:21]1>O1CCCC1>[Br:19][C:15]1[CH:14]=[C:13]([NH:12][C:6]2[C:5]3[C:10](=[CH:11][C:2]([NH:1][C:20]([CH:21]=[CH:22][C:23]([OH:25])=[O:24])=[O:26])=[CH:3][CH:4]=3)[N:9]=[CH:8][N:7]=2)[CH:18]=[CH:17][CH:16]=1

Komponenten

4

Edukt 2

HCID 7923Maleic AnhydrideHCID 53280457-Amino-4-[(3-bromophenyl)amino]quinazoline

Produkt 1

HCID 54170922HCID 54170922, VerbindungAusbeute 17,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a 5° C. solution of 0.158 g of 7-amino-4-(3-bromoanilino)-quinazoline (J Med Chem, 1995:3482) in 10 mL of tetrahydrofuran was added 0.059 g of maleic anhydride. The cold solution stirred for 15 minutes, and then the ice bath was removed. The reaction warmed to room temperature where it continued stirring for 15 hours. The suspension was heated under reflux for 30 minutes and then stirred at room temperature another 15 hours. Another 0.059 g of maleic anhydride and 20 mL of tetrahydrofuran were added, and the reaction was refluxed for an additional 2 hours. After another 15 hours at room temperature, the reaction was refluxed for 15 hours. The reaction was filtered, and the light tan solid was recrystallized first from dimethylformamide and then a second time from methanol to afford 0.036 g of the desired product.

Aufarbeitung

  1. customthe ice bath was removed
  2. stirringcontinued stirring for 15 hours
  3. temperatureThe suspension was heated
  4. temperatureunder reflux for 30 minutes
  5. stirringstirred at room temperature another 15 hours
  6. additionAnother 0.059 g of maleic anhydride and 20 mL of tetrahydrofuran were added
  7. temperaturethe reaction was refluxed for an additional 2 hours
  8. waitAfter another 15 hours at room temperature
  9. temperaturethe reaction was refluxed for 15 hours
  10. filtrationThe reaction was filtered
  11. customthe light tan solid was recrystallized first from dimethylformamide

Quellen und Nachweise

ORD-Eintrag
ord-9aac7f90ec064227b1a2c0d01673abd2
Quelldatensatz
uspto-grants-2002_02
Patentnummer
US06344459B1

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