Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | 1-cyclohexyl-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine | HCID 58009917 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | Ammonium Chloride | HCID 25517 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 50906783 | HCID 50906783 | 90% |
Reaction Steps
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)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09365579B2 |
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| Source dataset | uspto-grants-2016_06 |
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| ORD ID | ord-04c48399477a49aa98b4f866c9b3a48b |
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| Source note | uspto-grants-2016_06 |
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