Sodium Azide → HCID 86664796, Verbindung

HRID 2047219Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2047219
CS(O[CH:6]([C:8]1[CH:13]=[C:12]([N:14]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[N:11]2[N:31]=[CH:32][C:33]([C:34]3[CH:35]=[N:36][C:37]4[C:42]([CH:43]=3)=[CH:41][C:40]([F:44])=[CH:39][CH:38]=4)=[C:10]2[N:9]=1)[CH3:7])(=O)=O.C(N(CC)C(C)C)(C)C.[N-:54]=[N+:55]=[N-:56].[Na+]>CS(C)=O>[N:54]([CH:6]([C:8]1[CH:13]=[C:12]([N:14]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:29])([CH3:28])[CH3:30])[CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:20])([CH3:21])[CH3:22])[N:11]2[N:31]=[CH:32][C:33]([C:34]3[CH:35]=[N:36][C:37]4[C:42]([CH:43]=3)=[CH:41][C:40]([F:44])=[CH:39][CH:38]=4)=[C:10]2[N:9]=1)[CH3:7])=[N+:55]=[N-:56]

Komponenten

5

Edukt 3

HCID 33557Sodium AzideHCID 81531DiisopropylethylamineHCID 866647951-(7-(Bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(6-fluoroquinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)ethyl methanesulfonate

Produkt 1

HCID 86664796HCID 86664796, VerbindungAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To a solution of 1-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(6-fluoroquinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)ethyl methanesulfonate (6.8 g, 10.3 mmol) in DMSO (100 mL) and N,N-diisopropyl-ethylamine (8.95 mL, 51.4 mmol) was added sodium azide (2.0 g, 30.8 mmol). After 4 hours the reaction was complete by HPLC. The contents of the flask were transferred to a separatory funnel, washed twice with water and twice with brine. The organics were dried over sodium sulfate, filtered and concentrated in vacuo to afford 5-(1-azidoethyl)-3-(6-fluoroquinolin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (6.2 g; 99% yield) as a dark yellow oil. HPLC: 6.67 min (Method D). LCMS: No ion detected.

Aufarbeitung

  1. customThe contents of the flask were transferred to a separatory funnel
  2. washwashed twice with water and twice with brine
  3. dry with materialThe organics were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ef6ef774e1734a5bbdccd1d664f82705
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08591943B2

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