1-(8-ethyl-1,4-dioxaspiro[4.4]nonan-7-yl)-6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine → 1-(8-ethyl-1,4-dioxaspiro[4.4]nonan-7-yl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine

HRID 1969883Notes

Reaction equation

HRID 1969883 reaction equation
[CH2:1]([CH:3]1[CH2:11][C:6]2([O:10][CH2:9][CH2:8][O:7]2)[CH2:5][CH:4]1[C:12]1[N:16]2[C:17]3[CH:23]=[CH:22][N:21](S(C4C=CC(C)=CC=4)(=O)=O)[C:18]=3[N:19]=[CH:20][C:15]2=[N:14][N:13]=1)[CH3:2]>O1CCOCC1.[OH-].[Na+]>[CH2:1]([CH:3]1[CH2:11][C:6]2([O:7][CH2:8][CH2:9][O:10]2)[CH2:5][CH:4]1[C:12]1[N:16]2[C:17]3[CH:23]=[CH:22][NH:21][C:18]=3[N:19]=[CH:20][C:15]2=[N:14][N:13]=1)[CH3:2]

Participants

4

Reactant 1

HCID 585572181-(8-ethyl-1,4-dioxaspiro[4.4]nonan-7-yl)-6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine

Product 1

HCID 1360092531-(8-ethyl-1,4-dioxaspiro[4.4]nonan-7-yl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazineYield 88.1%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

To the solution of 1-(8-ethyl-1,4-dioxaspiro[4.4]nonan-7-yl)-6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine (3.76 g, 8.04 mmol) in 1,4-dioxane (55 mL), aqueous sodium hydroxide solution (2N, 12 mL) was added and the reaction mixture was heated at about 60° C. for about 90 min. The solvent was removed and the residue partitioned between saturated solution of ammonium chloride in water and EtOAc (75 mL each). The aqueous phase was further washed with EtOAc (60 mL); the combined organic extracts were washed with brine (65 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated to yield a brown solid. The solid was triturated in ether (20 mL) and the precipitate was collected by filtration and dried to yield 1-(8-ethyl-1,4-dioxaspiro[4.4]nonan-7-yl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine (2.22 g, 88%) as a beige solid. LC/MS (Table 1, Method a) Rt=1.71 min; MS m/z: 314 (M+H)+.

Workup

  1. customThe solvent was removed
  2. customthe residue partitioned between saturated solution of ammonium chloride in water and EtOAc (75 mL each)
  3. washThe aqueous phase was further washed with EtOAc (60 mL)
  4. washthe combined organic extracts were washed with brine (65 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto yield a brown solid
  9. customThe solid was triturated in ether (20 mL)
  10. filtrationthe precipitate was collected by filtration
  11. customdried

Sources & evidence

ORD record
ord-e236737de73943899a7656d037f8d8ea
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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