Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Diphenylphosphoryl azide | HCID 123414 | — |
| Reactant | HCID 67277247 | HCID 67277247 | — |
| Solvent | tert-Butanol | HCID 6386 | — |
| Product | HCID 15953425 | HCID 15953425 | — |
Reaction Steps
Diphenyl azidophosphate (0.083 mL) was added to 4-{[(1S,2R)-2-methylcyclohexyl]amino}-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (56 mg) and triethylamine (0.075 mL) in tert-butanol (1.5 mL) and the mixture was stirred at 100° C. for 4 hours. tert-butanol was removed under reduced pressure, then chloroform and water were added, and the organic layer was separated, washed with brine, and dried over MgSO4. After removal of MgSO4 and solvent, the residue was purified by column chromatography on silica gel with chloroform and methanol (98:2 to 90:10) to give 1-[(1S,2R)-2-methylcyclohexyl]-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2(1H)-one (53 mg) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08163767B2 |
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| Source dataset | uspto-grants-2012_04 |
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| ORD ID | ord-c310459d9d224d7d8761ec561d915ee1 |
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| Source note | uspto-grants-2012_04 |
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