Isobutylene oxide → HCID 58216647, compound

HRID 1799566Notes

Reaction equation

HRID 1799566 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[N:8]=[N:9][NH:10][C:5]2=[CH:4][CH:3]=1.[CH3:11][C:12]1([CH3:15])[CH2:14][O:13]1.CC(C)([O-])C.[K+]>CN(C=O)C.[Cl-].[NH4+]>[Cl:1][C:2]1[N:7]=[C:6]2[N:8]=[N:9][N:10]([CH2:11][C:12]([CH3:15])([OH:13])[CH3:14])[C:5]2=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11208Isobutylene oxideHCID 23665647Potassium tert-butoxideHCID 178477915HCID 178477915, compound

Product 1

HCID 58216647HCID 58216647, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
60 °C

Procedure

5-Chloro-1H-[1,2,3]triazolo[4,5-b]pyridine (Example 27, Step 1) (285 mg, 1.85 mmol) and 2,2-dimethyloxirane (0.18 mL, 1.94 mmol) were taken-up in DMF (7.4 mL) and potassium tert-butoxide (310 mg, 2.77 mmol) was added. The mixture was heated to 60° C. overnight and then to 85° C. for an additional 36 hours. The mixture was then cooled to room temperature, diluted with saturated aqueous ammonium chloride, and extracted with ethyl acetate (3×). The organic layers were combined, dried over anhydrous magnesium sulfate, filtered, concentrated in vacuo and purified via reverse phase HPLC (10-100% acetonitrile/water+0.05% TFA modifier). Desired fractions were lyophilized to afford the title compound as a yellow solid.

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. extractionextracted with ethyl acetate (3×)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. custompurified via reverse phase HPLC (10-100% acetonitrile/water+0.05% TFA modifier)

Sources & evidence

ORD record
ord-39f078e364ff4e2497457ffba3c59fa8
Source dataset
uspto-grants-2013_01
Patent number
US08344144B2

Reaction notes

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