Sodium Hydroxide → 8-cyclohexyl-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazine

HRID 2204540Notes

Reaction equation

HRID 2204540 reaction equation
[OH-].[Na+].[CH:3]1([C:9]2[N:13]3[C:14]4[CH:20]=[CH:19][N:18](S(C5C=CC(C)=CC=5)(=O)=O)[C:15]=4[N:16]=[CH:17][C:12]3=[N:11][CH:10]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1>O1CCOCC1>[CH:3]1([C:9]2[N:13]3[C:14]4[CH:20]=[CH:19][NH:18][C:15]=4[N:16]=[CH:17][C:12]3=[N:11][CH:10]=2)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 580098738-cyclohexyl-3-tosyl-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazine

Product 1

HCID 580102658-cyclohexyl-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazineYield 19.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Aqueous NaOH (2N, 0.3 mL) was added to 8-cyclohexyl-3-tosyl-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazine (0.051 g, 0.13 mmol) in 1,4-dioxane (3 mL) and the mixture was heated at reflux for about 1 h. The organic solvent was removed under reduced pressure and the aqueous phase neutralized with aqueous 1 N HCl and extracted with EtOAc (2×15 mL). The combined organic extracts were washed with brine (1×10 mL), dried over anhydrous MgSO4, and concentrated in vacuo. The residue was suspended in MeCN (2 mL) and the precipitate was collected by filtration and dried to yield 8-cyclohexyl-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazine as a tan solid (0.006 g, 19%): LC/MS (Table 2, Method a) Rt=2.12 min; MS m/z: 241 (M+H)+.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for about 1 h
  3. customThe organic solvent was removed under reduced pressure
  4. extractionextracted with EtOAc (2×15 mL)
  5. washThe combined organic extracts were washed with brine (1×10 mL)
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentrated in vacuo
  8. filtrationthe precipitate was collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-d35adcc5c40f495db8b316375a6f097f
Source dataset
uspto-grants-2016_06
Patent number
US09365579B2

Reaction notes

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