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Water → 2-(1-azidoethyl)-5-tosyl-5H-pyrrolo[2,3-b]pyrazine

HRID 2204481
Notes
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Reaction equation

HRID 2204481 reaction equation
[S:1]([N:11]1[C:15]2=[N:16][CH:17]=[C:18]([CH:20](O)[CH3:21])[N:19]=[C:14]2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].O=S(Cl)Cl.[N-:27]=[N+:28]=[N-:29].[Na+].O>C(Cl)Cl.CCOC(C)=O.C([O-])(O)=O.[Na+]>[N:27]([CH:20]([C:18]1[N:19]=[C:14]2[CH:13]=[CH:12][N:11]([S:1]([C:4]3[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=3)(=[O:3])=[O:2])[C:15]2=[N:16][CH:17]=1)[CH3:21])=[N+:28]=[N-:29]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 33557Sodium AzideHCID 580102001-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)ethanol

Product 1

HCID 580101502-(1-azidoethyl)-5-tosyl-5H-pyrrolo[2,3-b]pyrazineYield 100.4%

Reagents, catalysts & solvents 3

HCID 6344
Dichloromethane
Solvent
HCID 8857Ethyl AcetateSolvent2×
HCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 1-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)ethanol (0.600 g, 1.89 mmol) in DCM (10 mL) was added SOCl2 (0.690 mL, 9.45 mmol) at ambient temperature. After about 4 h the reaction mixture was diluted with EtOAc (50 mL) and saturated aqueous NaHCO3 (50 mL) was added to the reaction mixture. After gas evolution ceased, the organic layer was separated, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was dissolved in DMF (10 mL) and sodium azide (0.615 g, 9.45 mmol) was added to the reaction mixture. After about 15 h, EtOAc (50 mL) and water (50 mL) were added to the reaction mixture. The organic layer was separated, concentrated under reduced pressure, and purified by silica gel chromatography eluting with 20-80% EtOAc/heptane to provide 2-(1-azidoethyl)-5-tosyl-5H-pyrrolo[2,3-b]pyrazine (0.65 g, 100%) as a colorless solid: LC/MS (Table 2, Method a) Rt=2.67 min; MS m/z: 343 (M+H)+.

Workup

  1. additionwas added to the reaction mixture
  2. customthe organic layer was separated
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was dissolved in DMF (10 mL)
  7. customThe organic layer was separated
  8. concentrationconcentrated under reduced pressure
  9. custompurified by silica gel chromatography
  10. washeluting with 20-80% EtOAc/heptane

Sources & evidence

ORD record
ord-7bc58771336a4bc495e4cb9395fd3888
Source dataset
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09365579B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes