HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → tert-butyl (1S,2R)-2-(5-bromo-4-cyano-2-fluorophenylamino)cyclohexylcarbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | (1S,2R)-Cyclohexane-1,2-diamine, N1-BOC protected | HCID 1514389 | — |
| Reactant | 2-Bromo-4,5-difluorobenzonitrile | HCID 19261277 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | tert-butyl (1S,2R)-2-(5-bromo-4-cyano-2-fluorophenylamino)cyclohexylcarbamate | HCID 69283992 | 93.4% |
Reaction Steps
A solution of 2-bromo-4,5-difluorobenzonitrile (218 mg, 1.00 mmol), tert-butyl (1S,2R)-2-aminocyclohexylcarbamate (214 mg, 1.00 mmol) and DIEA (0.300 mL, 1.72 mmol) in DMSO (2 mL) was stirred at 100 C for 18 h. Water was added to induce precipitation. The precipitate was collected and dried on vacuum to give tert-butyl (1S,2R)-2-(5-bromo-4-cyano-2-fluorophenylamino)cyclohexylcarbamate as a solid (385 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09359375B2 |
| Source dataset | uspto-grants-2016_06 |
| ORD ID | ord-982e17e6b51f453aa2dad71c3e8acefe |
| Source note | uspto-grants-2016_06 |