HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → (R)-2-(4-cyano-3,5-difluorophenylamino)-4-methylpentanamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 2,4,6-Trifluorobenzonitrile | HCID 737177 | — |
| Reactant | (R)-2-Amino-4-methylpentanamide hydrochloride | HCID 56776963 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | (R)-2-(4-cyano-3,5-difluorophenylamino)-4-methylpentanamide | HCID 67509019 | 26.1% |
Reaction Steps
To a solution of 2,4,6-trifluorobenzonitrile (208 mg, 1.32 mmol) in DMSO (2 mL), a solution of D-leucine amide hydrochloride (220 mg, 1.32 mmol) and DIEA (0.688 mL, 3.96 mmol) in DMSO (5 mL) was added. After being stirred at room temperature for 18 h, water and EtOAc were added. The organic phase was separated, washed with water, dried over Na2SO4, concentrated in vacuo. The residue was purified by a silica gel column, eluted with 20-80% EtOAc in hexane to give (R)-2-(4-cyano-3,5-difluorophenylamino)-4-methylpentanamide (92 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09359375B2 |
| Source dataset | uspto-grants-2016_06 |
| ORD ID | ord-a5e14c12274847e1ab85fbded44b6354 |
| Source note | uspto-grants-2016_06 |