Hydrochloric Acid → 5-Chloropyrazine-2-carbohydrazide

HRID 1889002Notes

Reaction equation

HRID 1889002 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:8]([NH:10][NH:11]C(OC(C)(C)C)=O)=[O:9])=[N:6][CH:7]=1.Cl>O1CCOCC1>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:8]([NH:10][NH2:11])=[O:9])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 86666738HCID 86666738, compound

Product 1

HCID 457897975-Chloropyrazine-2-carbohydrazide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent3×

Procedure

To a solution of 1,1-dimethylethyl 2-[(5-chloro-2-pyrazinyl)carbonyl]hydrazine carboxylate (I48) (2.182 g, 8 mmol) in 1,4-dioxane (20 mL) was added 4M HCl in 1,4-dioxane (20.00 mL, 80 mmol). The solution was then stirred under argon for 4 hours. Analysis by LCMS showed some sign of starting material still present thus 4M HCl in 1,4-dioxane (8.00 mL, 32.0 mmol) was added. The solvent was then evaporated in vacuo and the remaining solid was loaded onto an SCX cartridge (2×10 g). The solid was then washed with methanol (2×30 mL) before being eluted from the cartridge by 2M NH3/MeOH. TLC confirmed product location and the solvent from the combined fractions was evaporated in vacuo. The solid was triturated with diethyl ether, filtered, and washed with diethyl ether to afford product in 1.02 g.

Workup

  1. additionwas added
  2. customThe solvent was then evaporated in vacuo
  3. washThe solid was then washed with methanol (2×30 mL)
  4. washbefore being eluted from the cartridge by 2M NH3/MeOH
  5. customthe solvent from the combined fractions was evaporated in vacuo
  6. customThe solid was triturated with diethyl ether
  7. filtrationfiltered
  8. washwashed with diethyl ether
  9. customto afford product in 1.02 g

Sources & evidence

ORD record
ord-0d63b09ce26d4dedbc08389d95032263
Source dataset
uspto-grants-2013_08
Patent number
US08501946B2

Reaction notes

Loading…