Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Phthalimide | HCID 6809 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | ethyl N-ethoxycarbonyliminocarbamate | HCID 220568 | — |
| Reactant | HCID 118214745 | HCID 118214745 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 118214746 | HCID 118214746 | 58.9% |
Reaction Steps
A mixture of tert-butyl ((1S)-1-(6-(3-hydroxypyrrolidin-1-yl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)carbamate (250 mg, 0.694 mmol), isoindoline-1,3-dione (153 mg, 1.04 mmol) and PPh3 (328 g, 1.25 mmol) in THF (2 mL) was stirred at 0° C. Next, diethyl azodicarboxylate (217 mg, 1.25 mmol) was added dropwise at 0° C. and the mixture was stirred at 20° C. for 16 hours. The solvent was evaporated in vacuo, and the residue was purified by preparative TLC to give the title compound as a white solid (200 mg, 42.3%). ESI-MS m/z [M+H]+ calc'd for C22H31N5O4, 490. found 490.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09371321B2 |
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| Source dataset | uspto-grants-2016_06 |
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| ORD ID | ord-141101345c004fc2884e2b09a25aa883 |
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| Source note | uspto-grants-2016_06 |
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