Sodium Hydroxide → HCID 50906783, compound

HRID 2204546Notes

Reaction equation

HRID 2204546 reaction equation
[CH:1]1([C:7]2[N:11]3[C:12]4[CH:18]=[CH:17][N:16](S(C5C=CC(C)=CC=5)(=O)=O)[C:13]=4[N:14]=[CH:15][C:10]3=[CH:9][N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>O1CCOCC1.CCOC(C)=O.[NH4+].[Cl-]>[CH:1]1([C:7]2[N:11]3[C:12]4[CH:18]=[CH:17][NH:16][C:13]=4[N:14]=[CH:15][C:10]3=[CH:9][N:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 580099171-cyclohexyl-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine

Product 1

HCID 50906783HCID 50906783, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 1-cyclohexyl-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine (0.020 g, 0.051 mmol) in 1,4-dioxane (3 mL) was added aqueous NaOH (2 N, 0.380 mL, 0.760 mmol). The reaction mixture was heated to about 90° C. After about 5 h, the reaction mixture was cooled to ambient temperature and diluted with EtOAc (10 mL) and saturated aqueous NH4Cl (10 mL). The organic layer was separated and washed with water (10 mL) followed by brine (10 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to provide 1-cyclohexyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine as a tan solid (0.011 g, 90%): LC/MS (Table 2, Method a) Rt=1.92 min; MS m/z: 241 (M+H)+.

Workup

  1. temperaturethe reaction mixture was cooled to ambient temperature
  2. customThe organic layer was separated
  3. washwashed with water (10 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-04c48399477a49aa98b4f866c9b3a48b
Source dataset
uspto-grants-2016_06
Patent number
US09365579B2

Reaction notes

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