Hydrochloric Acid → 3-(2-Ethylpyrid-3-ylamino)-6-methyl-1-(carboxymethyl)pyrazinone

HRID 398389Notes

Reaction equation

HRID 398389 reaction equation
[CH2:1]([C:3]1[C:8]([NH:9][C:10]2[C:11](=[O:23])[N:12]([CH2:17][C:18]([O:20]CC)=[O:19])[C:13]([CH3:16])=[CH:14][N:15]=2)=[CH:7][CH:6]=[CH:5][N:4]=1)[CH3:2].CO.[OH-].[Na+].Cl>O>[CH2:1]([C:3]1[C:8]([NH:9][C:10]2[C:11](=[O:23])[N:12]([CH2:17][C:18]([OH:20])=[O:19])[C:13]([CH3:16])=[CH:14][N:15]=2)=[CH:7][CH:6]=[CH:5][N:4]=1)[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 230001643-(2-Ethylpyrid-3-ylamino)-6-methyl-1-(ethoxycarbonylmethyl)pyrazinone

Product 1

HCID 230002023-(2-Ethylpyrid-3-ylamino)-6-methyl-1-(carboxymethyl)pyrazinoneYield 73.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 3-(2-Ethylpyrid-3-ylamino)-6-methyl-1-(ethoxycarbonylmethyl)pyrazinone (0.058 g, 0.183 mMol) from step 3 above in 6 mL of 1:1:1-tetrahydrofuran:methanol:water was added 183 μL (0.183 mMol) of 1N sodium hydroxide solution. The solution was stirred at ambient temperature for 18 h at which time 183 μL (0.183 mMol) of 1N hydrochloric acid solution was added. The solution was concentrated in vacuo several times from methanol and the residue was triturated with diethyl ether. The resulting precipitate was filtered off to afford the title compound as a beige powder (0.039 g; HPLC RT=3.13 min, method A).

Workup

  1. additionwas added
  2. concentrationThe solution was concentrated in vacuo several times from methanol
  3. customthe residue was triturated with diethyl ether
  4. filtrationThe resulting precipitate was filtered off

Sources & evidence

ORD record
ord-b8f4923dc0dc4367bf2a218e6c688d81
Source dataset
uspto-grants-2003_08
Patent number
US06610692B1

Reaction notes

Loading…