Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | Ammonium Hydroxide | HCID 14923 | — |
| Reactant | HCID 58382163 | HCID 58382163 | — |
| Solvent | Acetone | HCID 180 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 58382074 | HCID 58382074 | 60.1% |
Reaction Steps
1-Ethyl-2-(4-(2-methyl-1,3-dioxolan-2-yl)phenyl)-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-dipyrrolo[1,2-a:2′,3′-e]pyrazine (0.194 g, 0.406 mmol) was dissolved in acetone (6 mL) then treated with concentrated aqueous HCl (36 wt %, 0.170 mL, 2.08 mmol). The mixture was stirred at rt for 30 min. The solvents were evaporated under reduced pressure and then the material was treated with DCM (3 mL) and TFA (1.5 mL, 19 mmol). The mixture was stirred at rt for about 15 min then the solvents were evaporated under reduced pressure. The residue was dissolved in 1,4-dioxane (4 mL) then treated with concentrated aqueous NH4OH (26 wt %, 2 mL, 13.87 mmol). The mixture was stirred at rt for 30 min then warmed to about 50° C. for about 15 min. The mixture was cooled to rt and the solvents removed under reduced pressure. The material was treated with water (15 mL) then stirred for about 5 min at rt. The solids were collected by filtration then dried under vacuum at about 60° C. to a constant weight to give 1-(4-(1-ethyl-3H-dipyrrolo[1,2-a:2′,3′-e]pyrazin-2-yl)phenyl)ethanone (0.074 g, 60%): LC/MS (Table 2, Method b) Rt=2.37 min; MS m/z 304 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08785639B2 |
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| Source dataset | uspto-grants-2014_07 |
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| ORD ID | ord-1f9ec83d09c6454691102382b749fcc5 |
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| Source note | uspto-grants-2014_07 |
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