Isopropylamine → HCID 68675444, compound

HRID 2233026Notes

Reaction equation

HRID 2233026 reaction equation
C[O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[N:11]=[C:12](Cl)[C:13]3[N:14]([C:16](=[O:23])[N:17]([C:19]([CH3:22])([CH3:21])[CH3:20])[N:18]=3)[CH:15]=2)[CH:5]=1.[CH:26]([NH2:29])([CH3:28])[CH3:27]>C1COCC1.CCOC(C)=O>[C:19]([N:17]1[C:16](=[O:23])[N:14]2[CH:15]=[C:10]([C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=3)[C:3]([OH:2])=[O:25])[N:11]=[C:12]([NH:29][CH:26]([CH3:28])[CH3:27])[C:13]2=[N:18]1)([CH3:21])([CH3:20])[CH3:22]

Participants

5

Reactant 2

HCID 6363IsopropylamineHCID 68677920HCID 68677920, compound

Product 1

HCID 68675444HCID 68675444, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 580 mg of 3-(2-tert-butyl-8-chloro-3-oxo-2,3-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-6-yl)-benzoic acid methyl ester and 944 mg of isopropylamine in THF (8.0 mL) was stirred at ambient temperature. After 72 h, the reaction was diluted with EtOAc and washed with water followed by sat. sodium chloride solution. The organic layer was dried over sodium sulfate, filtered, and concentrated to an orange semi-solid. This material was dissolved in 1,4-dioxane (6.0 mL) and 2N KOH (1.0 mL) was added. This mixture was heated at reflux for 16 h, cooled to ambient temperature and the solvent removed. The residue was dissolved in water and the pH adjusted to 3 with 2N HCl prior to extraction with 9:1 chloroform/MeOH (3×). The organic extracts were washed with sat. sodium chloride solution, dried over sodium sulfate, filtered, and concentrated to leave 3-(2-tert-butyl-8-isopropylamino-3-oxo-2,3-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-6-yl)-benzoic acid as a yellow solid. MS (M+H+)=370.4.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to an orange semi-solid
  5. dissolutionThis material was dissolved in 1,4-dioxane (6.0 mL)
  6. addition2N KOH (1.0 mL) was added
  7. temperatureThis mixture was heated
  8. temperatureat reflux for 16 h
  9. customthe solvent removed
  10. dissolutionThe residue was dissolved in water
  11. extractionto extraction with 9:1 chloroform/MeOH (3×)
  12. washThe organic extracts were washed with sat. sodium chloride solution
  13. dry with materialdried over sodium sulfate
  14. filtrationfiltered
  15. concentrationconcentrated

Sources & evidence

ORD record
ord-fb87bea133bd4f64894042422c716303
Source dataset
uspto-grants-2010_05
Patent number
US07709473B2

Reaction notes

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