Boron tribromide → HCID 57717495, Verbindung

HRID 1984500Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1984500
B(Br)(Br)Br.[NH2:5][C:6]1[C:15]2=[N:16][N:17]([CH2:24][CH2:25][O:26]C)[C:18]([CH2:19][C:20]([CH3:23])([OH:22])[CH3:21])=[C:14]2[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:7]=1>ClCCl>[NH2:5][C:6]1[C:15]2=[N:16][N:17]([CH2:24][CH2:25][OH:26])[C:18]([CH2:19][C:20]([CH3:23])([OH:22])[CH3:21])=[C:14]2[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:7]=1

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 57717561HCID 57717561, Verbindung

Produkt 1

HCID 57717495HCID 57717495, VerbindungAusbeute 24,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Under a nitrogen atmosphere, boron tribromide (6 mL of a 1 M solution in dichloromethane) was added to a solution of 1-[4-amino-2-(2-methoxyethyl)-2H-pyrazolo[3,4-c]quinolin-1-yl]-2-methylpropan-2-ol (0.500 g, 1.59 mmol) in dichloromethane (8 mL), and the reaction was stirred for four hours. The dichloromethane was removed under reduced pressure, and the residue was dissolved in a mixture of ethanol and 3 N hydrochloric acid. A solution of 7 N ammonia in methanol was added, and then the solvent was removed under reduced pressure. The treatment with ammonia and the concentration were repeated two more times. The crude product was purified by chromatography using a HORIZON HPFC system (40+M cartridge, eluting with 0-30% CMA in chloroform) followed by trituration with acetonitrile and recrystallization from acetonitrile to provide 115 mg of 1-[4-amino-2-(2-hydroxyethyl)-2H-pyrazolo[3,4-c]quinolin-1-yl]-2-methylpropan-2-ol as white crystals, mp 196-198° C.

Aufarbeitung

  1. customThe dichloromethane was removed under reduced pressure
  2. dissolutionthe residue was dissolved in a mixture of ethanol and 3 N hydrochloric acid
  3. additionA solution of 7 N ammonia in methanol was added
  4. customthe solvent was removed under reduced pressure
  5. concentrationThe treatment with ammonia and the concentration
  6. customThe crude product was purified by chromatography
  7. washa HORIZON HPFC system (40+M cartridge, eluting with 0-30% CMA in chloroform)
  8. customfollowed by trituration with acetonitrile and recrystallization from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-77d357c3aaa74f1ea51be7e53bdfb76b
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07544697B2

Notizen zur Reaktion

Wird geladen…