Hydrochloric Acid → HCID 69414988, compound

HRID 1270149Notes

Reaction equation

HRID 1270149 reaction equation
Cl[C:2]1[C:3]2[N:4]([C:13]([O:16]C)=[N:14][N:15]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[C:7]([F:12])[CH:6]=2.Cl.[CH2:19]([O:21][C:22](=[O:25])[CH2:23][NH2:24])[CH3:20].C(N(CC)CC)C.Cl>CN(C=O)C.C(O)C(F)(F)F.O1CCOCC1>[CH2:19]([O:21][C:22](=[O:25])[CH2:23][NH:24][C:2]1[C:3]2[N:4]([C:13](=[O:16])[NH:14][N:15]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[C:7]([F:12])[CH:6]=2)[CH3:20]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 2723640Glycine ethyl ester, hydrochlorideHCID 14783667HCID 14783667, compound

Product 1

HCID 69414988HCID 69414988, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 64092,2,2-TrifluoroethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 152 mg of 4-chloro-8-fluoro-1-methoxy-[1,2,4]triazolo[4,3-a]quinoxaline, 127 mg of glycine ethyl ester hydrochloride, and 602 mg of triethylamine in DMF (4.0 mL) was stirred at room temperature for 41 hrs. The reaction mixture was concentrated, dissolved in 25% IPA/methylene chloride and washed with 50% saturated sodium bicarbonate, and then water. The organic emulsion was collected and concentrated to provide a yellow solid. A solution of this solid in trifluoroethanol (10 mL) was treated with 5 equiv. of 4.0 N HCl in dioxane for 15 min., and the mixture was concentrated. The residue was dissolved in 20% IPA/methylene chloride, and washed with 50% saturated sodium bicarbonate, and then water. The organic emulsion was collected and concentrated to provide a yellow solid which was triturated. The resulting off-white solid was collected, dried, washed with ether and dried to provide the title compound. MS (M+H)+=306.0.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutiondissolved in 25% IPA/methylene chloride
  3. washwashed with 50% saturated sodium bicarbonate
  4. customThe organic emulsion was collected
  5. concentrationconcentrated
  6. customto provide a yellow solid
  7. concentrationthe mixture was concentrated
  8. dissolutionThe residue was dissolved in 20% IPA/methylene chloride
  9. washwashed with 50% saturated sodium bicarbonate
  10. customThe organic emulsion was collected
  11. concentrationconcentrated
  12. customto provide a yellow solid which
  13. customwas triturated
  14. customThe resulting off-white solid was collected
  15. customdried
  16. washwashed with ether
  17. customdried

Sources & evidence

ORD record
ord-48a95ffcf5704e23a270e92f0b49f15d
Source dataset
uspto-grants-2007_04
Patent number
US07202245B2

Reaction notes

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