Sodium Azide → HCID 86664796, compound

HRID 2369019Notes

Reaction equation

HRID 2369019 reaction equation
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]

Participants

5

Reactant 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

Product 1

HCID 86664796HCID 86664796, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-37ae56601a3b42dbab0ed423dfa84af1
Source dataset
uspto-grants-2014_04
Patent number
US08703784B2

Reaction notes

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