Sodium Azide → HCID 89619119, compound

HRID 1502157Notes

Reaction equation

HRID 1502157 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N:6][CH:7]=1.C(O[CH2:23][CH3:24])(OCC)(OCC)C.[N-:25]=[N+:26]=[N-:27].[Na+]>C(O)(=O)C>[CH3:24][C:23]1[N:1]([C:2]2[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N:6][CH:7]=2)[N:27]=[N:26][N:25]=1

Participants

5

Reactant 3

HCID 33557Sodium Azide2×HCID 66221Triethyl orthoacetate2×HCID 21876034Ethyl 2-(5-aminopyridin-2-yl)acetate

Product 1

HCID 89619119HCID 89619119, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

Ethyl 2-(5-aminopyridin-2-yl)acetate (1.314 g, 7.29 mmol) dissolved in acetic acid (24.31 ml) and added triethyl orthoacetate (2.69 ml, 14.58 mmol) and sodium azide (0.881 g, 13.55 mmol). The reaction was stirred at 80° C. for 3 hrs. When LC-MS showed reaction was not complete, added more triethyl orthoacetate (2.69 ml, 14.58 mmol) and sodium azide (0.881 g, 13.55 mmol) then continued heating at 80° C. overnight. Evaporated off acetic acid then diluted with ethyl acetate and washed with saturated NaHCO3 solution, brine, then dried over Na2SO4, filtered and concentrated. The crude material was purified by chromatography through an ISCO 40 g Redi-sep column and eluting with 5% MeOH/DCM to yield title compound: LC-MS: M+1=248

Workup

  1. customreaction
  2. temperaturethen continued heating at 80° C. overnight
  3. customEvaporated off acetic acid
  4. additionthen diluted with ethyl acetate
  5. washwashed with saturated NaHCO3 solution, brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude material was purified by chromatography through an ISCO 40 g Redi-sep column
  10. washeluting with 5% MeOH/DCM

Sources & evidence

ORD record
ord-8d1cfa445bc8429094b444ad4c58c430
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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