Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Trifluoromethanesulfonic anhydride | HCID 67749 | — |
| Reactant | 1,8-Diazabicyclo(5.4.0)undec-7-ene | HCID 81184 | — |
| Reactant | HCID 178526347 | HCID 178526347 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 178511230 | HCID 178511230 | 59% |
Reaction Steps
trans-4-(7H-Pyrrolo[3,2-e][1,2,3]triazolo[1,5-c]pyrimidin-1-yl)cyclohexanecarbaldehyde oxime (37.4 mg, 0.132 mmol) in dichloromethane (3 mL) was mixed with trifluoromethanesulfonic anhydride (24.0 μL, 0.145 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (43.0 μL, 0.289 mmol) and stirred at room temperature for 18 hours. After addition of water, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/2 (v/v)) and washed with hexane/ethyl acetate (5/1 (v/v)) to give the title compound as a colorless solid (20.7 mg, yield 59%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09216999B2 |
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| Source dataset | uspto-grants-2015_12 |
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| ORD ID | ord-c698a913a2d94922b0985c0294e023f8 |
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| Source note | uspto-grants-2015_12 |
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