Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl isocyanate | HCID 8022 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | HCID 57344512 | HCID 57344512 | — |
| Product | HCID 57344635 | HCID 57344635 | 83.2% |
Reaction Steps
To a round bottomed flask was added 6-(4-chlorophenyl)-1-methyl-4H-benzo[c]isoxazolo[4,5-e]azepin-4-amine (218 mg, 0.67 mmol). The flask was purged with nitrogen, MeCN was added (7 mL), and the solution was cooled to 0° C. Ethyl isocyanate (128 μL, 1.62 mmol) and triethylamine (244 μL, 1.75 mmol) were added and the reaction was allowed to warm to ambient temperature and stirred for 2 h. The reaction was quenched with a 1:1 mixture of sat. aq. NaHCO3:brine and extracted with EtOAc. The organic layer was dried over Na2SO4, filtered, concentrated and purified on a Biotage (isocratic elution 40% EtOAc: 60% Hexanes) to provide the title compound as white solid (220 mg). LC/MS m/z 395 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08796261B2 |
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| Source dataset | uspto-grants-2014_08 |
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| ORD ID | ord-e636b0cbc297419ab71fe54fb28b2aea |
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| Source note | uspto-grants-2014_08 |
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