Hydrochloric Acid → HCID 68675905, compound

HRID 2233024Notes

Reaction equation

HRID 2233024 reaction equation
[C:1]([N:5]1[C:24](=[O:25])[N:8]2[CH:9]=[C:10]([C:17]([CH3:23])([CH3:22])[C:18]([O:20]C)=[O:19])[N:11]=[C:12]([NH:13][CH:14]([CH3:16])[CH3:15])[C:7]2=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].Cl>O1CCOCC1.O>[C:1]([N:5]1[C:24](=[O:25])[N:8]2[CH:9]=[C:10]([C:17]([CH3:23])([CH3:22])[C:18]([OH:20])=[O:19])[N:11]=[C:12]([NH:13][CH:14]([CH3:15])[CH3:16])[C:7]2=[N:6]1)([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 68676946HCID 68676946, compound

Product 1

HCID 68675905HCID 68675905, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 400 mg of methyl 2-(2-tert-butyl-8-isopropylamino-3-oxo-2,3-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-6-yl)-2-methyl-propionate in dioxane (10.0 mL) was added 6.0 N KOH (1.0 mL) and the mixture was heated at reflux for 16 h. The reaction mixture was cooled to ambient temperature, diluted with water, the pH was adjusted to 2.0 with 6.0 N HCl, and the mixture was extracted with EtOAc (2×). The organic extracts were dried over magnesium sulfate, filtered, and concentrated to leave 2-(2-tert-butyl-8-isopropylamino-3-oxo-2,3-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-6-yl)-2-methyl-propionic acid as a white solid. MS (M+H+)=336.3.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 16 h
  3. extractionthe mixture was extracted with EtOAc (2×)
  4. dry with materialThe organic extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d099f9d81fb84af4b0f46a68d97e015f
Source dataset
uspto-grants-2010_05
Patent number
US07709473B2

Reaction notes

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