Boron tribromide → HCID 66826071, Verbindung

HRID 1468619Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1468619
[NH2:1][N:2]1[C:10]2[C:6]([N:7]3[N:13]([CH2:14][CH2:15][O:16]C)[C:12](=[O:18])[N:11]([CH2:19][CH2:20][N:21]4[CH2:26][CH2:25][N:24]([C:27]5[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=5)[CH2:23][CH2:22]4)[CH:8]3[N:9]=2)=[C:5]([C:34]2[O:35][CH:36]=[CH:37][CH:38]=2)[N:4]=[CH:3]1.B(Br)(Br)Br>C(Cl)Cl>[NH2:1][N:2]1[C:10]2[C:6]([N:7]3[N:13]([CH2:14][CH2:15][OH:16])[C:12](=[O:18])[N:11]([CH2:19][CH2:20][N:21]4[CH2:22][CH2:23][N:24]([C:27]5[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=5)[CH2:25][CH2:26]4)[CH:8]3[N:9]=2)=[C:5]([C:34]2[O:35][CH:36]=[CH:37][CH:38]=2)[N:4]=[CH:3]1

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 66826048HCID 66826048, Verbindung

Produkt 1

HCID 66826071HCID 66826071, VerbindungAusbeute 10,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of compound 5-amino-3-[2-[4-(4-fluorophenyl)piperazin-1-yl]ethyl]-8-(2-furyl)-1-(2-methoxyethyl)-[1,2,4]triazolo[5,1-f]purin-2-one (Example I2) (0.050 g, 0.095 mmol), in DCM (3 ml) was added BBr3 (0.1 ml, 0.105 mmol) drop wise at 0° C. and stirred at 25° C. for 20 hours. The reaction mixture was quenched with sat. NaHCO3 (25 ml) and extracted with DCM (3×20 ml). The crude product was purified by LCMS to obtain 5-Amino-3-[2-[4-(4-fluorophenyl)piperazin-1-yl]ethyl]-8-(2-furyl)-1-(2-hydroxyethyl)-[1,2,4]triazolo[5,1-f]purin-2-one (5 mg, 10%) as an off white solid

Aufarbeitung

  1. customwise at 0° C.
  2. customThe reaction mixture was quenched with sat. NaHCO3 (25 ml)
  3. extractionextracted with DCM (3×20 ml)
  4. customThe crude product was purified by LCMS

Quellen und Nachweise

ORD-Eintrag
ord-e9a3a095d6164fe2bb6a5e14bd00158f
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006177B2

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