Boron tribromide → HCID 66826635, Verbindung

HRID 1468615Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1468615
[NH2:1][N:2]1[C:10]2[C:6]([N:7]3[N:13]([CH3:14])[C:12](=[O:15])[N:11]([CH2:16][CH2:17][N:18]4[CH2:23][CH2:22][N:21]([C:24]5[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][O:33]C)=[CH:26][CH:25]=5)[CH2:20][CH2:19]4)[CH:8]3[N:9]=2)=[C:5]([C:35]2[O:36][CH:37]=[CH:38][CH:39]=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]([CH3:14])[C:12](=[O:15])[N:11]([CH2:16][CH2:17][N:18]4[CH2:23][CH2:22][N:21]([C:24]5[CH:25]=[CH:26][C:27]([O:30][CH2:31][CH2:32][OH:33])=[CH:28][CH:29]=5)[CH2:20][CH2:19]4)[CH:8]3[N:9]=2)=[C:5]([C:35]2[O:36][CH:37]=[CH:38][CH:39]=2)[N:4]=[CH:3]1

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 66824629HCID 66824629, Verbindung

Produkt 1

HCID 66826635HCID 66826635, VerbindungAusbeute 95,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of compound 5-amino-8-(2-furyl)-3-[2-[4-[4-(2-methoxyethoxy)phenyl]piperazin-1-yl]ethyl]-1-methyl-[1,2,4]triazolo[5,1-f]purin-2-one (Example A1) (0.075 g, 0.140 mmol), in DCM (10 ml) was added BBr3 (0.15 ml, 0.154 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 column chromatography to obtain 5-amino-8-(2-furyl)-3-[2-[4-[4-(2-hydroxyethoxy)phenyl]piperazin-1-yl]ethyl]-1-methyl-[1,2,4]triazolo[5,1-f]purin-2-one (70 mg, 90%) as an off white solid

Aufarbeitung

  1. customThe reaction mixture was quenched with sat. NaHCO3 (25 ml)
  2. extractionextracted with DCM (3×20 ml)
  3. customThe crude product was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3e5062cd288a403c80904c247150d094
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006177B2

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