Azidotrimethylsilane → HCID 178520835, compound

HRID 1893455Notes

Reaction equation

HRID 1893455 reaction equation
[C:1]([C:3]1[N:7]2[C:8]3[C:13]([N:14]=[C:15]([NH:16][CH2:17][CH2:18][CH2:19][OH:20])[C:6]2=[N:5][CH:4]=1)=[CH:12][C:11]([C:21]([F:24])([F:23])[F:22])=[CH:10][CH:9]=3)#[CH:2].C[Si]([N:29]=[N+:30]=[N-:31])(C)C>CO>[NH:29]1[C:1]([C:3]2[N:7]3[C:8]4[C:13]([N:14]=[C:15]([NH:16][CH2:17][CH2:18][CH2:19][OH:20])[C:6]3=[N:5][CH:4]=2)=[CH:12][C:11]([C:21]([F:22])([F:23])[F:24])=[CH:10][CH:9]=4)=[CH:2][N:31]=[N:30]1

Participants

4

Reactant 2

HCID 78378AzidotrimethylsilaneHCID 59333283HCID 59333283, compound

Product 1

HCID 178520835HCID 178520835, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of the 3-{[1-ethynyl-7-(trifluoromethyl)imidazo[1,2-a]quinoxalin-4-yl]amino}propan-1-ol as prepared in example 30 (20 mg, 0.06 mmol) in neat trimethylsilylazide (200 μL) was stirred at 100° C. for 65 h in a reaction vial. The reaction mixture was then stirred at 105° C. for 24 h to go to completion, and was then allowed to cool to room temperature, diluted in methanol (2 mL) and concentrated under vacuum. The crude product was purified by preparative TLC (silica gel, dichloromethane/methanol 90/10) to afford a solid. Further purification by washing with dichloromethane afforded the title compound (3 mg, 13%) as a yellow solid.

Workup

  1. stirringThe reaction mixture was then stirred at 105° C. for 24 h
  2. temperatureto cool to room temperature
  3. concentrationconcentrated under vacuum
  4. customThe crude product was purified by preparative TLC (silica gel, dichloromethane/methanol 90/10)
  5. customto afford a solid
  6. customFurther purification
  7. washby washing with dichloromethane

Sources & evidence

ORD record
ord-4c2f13c3da5742e7a6310a311f7ac96e
Source dataset
uspto-grants-2013_08
Patent number
US08513250B2

Reaction notes

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