Sodium Hydroxide → HCID 136198858, compound

HRID 1854386Notes

Reaction equation

HRID 1854386 reaction equation
[CH:1]1([C:7]2[N:8]=[C:9]3[CH:14]=[N:13][C:12]4[N:15](S(C5C=CC(C)=CC=5)(=O)=O)[CH:16]=[CH:17][C:11]=4[N:10]3[CH:28]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>O1CCOCC1>[CH:1]1([C:7]2[N:8]=[C:9]3[CH:14]=[N:13][C:12]4[NH:15][CH:16]=[CH:17][C:11]=4[N:10]3[CH:28]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58009935HCID 58009935, compound

Product 1

HCID 136198858HCID 136198858, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

7-Cyclohexyl-3-tosyl-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazine (0.13 g, 0.33 mmol) was dissolved in 1,4-dioxane (5 mL) and aqueous NaOH (2N, 0.5 mL) was added. The mixture was heated at reflux for about 30 min. The organic solvent was removed under reduced pressure. The aqueous phase was neutralized with 1 N aqueous HCl and extracted with EtOAc (2×25 mL). The combined organic extracts were washed with brine (15 mL), dried over anhydrous MgSO4, and concentrated under reduced pressure. The residue was purified by RP-HPLC (Table 2, Method h) to yield 7-cyclohexyl-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazine as an off-white solid (0.011 g, 14%): LC/MS (Table 2, Method a) Rt=2.06 min; MS m/z: 241 (M+H)+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for about 30 min
  3. customThe organic solvent was removed under reduced pressure
  4. extractionextracted with EtOAc (2×25 mL)
  5. washThe combined organic extracts were washed with brine (15 mL)
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by RP-HPLC (Table 2, Method h)

Sources & evidence

ORD record
ord-6b6d60b2e67944f995f0e7b1894aef94
Source dataset
uspto-grants-2015_02
Patent number
US08962629B2

Reaction notes

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