HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → (R)-2-(5-bromo-4-cyano-2-fluorophenylamino)-3-methoxypropanamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 2-Bromo-4,5-difluorobenzonitrile | HCID 19261277 | — |
| Reactant | (R)-2-amino-3-methoxypropanamide hydrochloride | HCID 86666156 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | (R)-2-(5-bromo-4-cyano-2-fluorophenylamino)-3-methoxypropanamide | HCID 67508869 | 21.4% |
Reaction Steps
A solution of 2-bromo-4,5-difluorobenzonitrile (168 mg, 0.770 mmol), (R)-2-amino-3-methoxypropanamide hydrochloride (120 mg, 0.776 mmol) and DIEA (0.500 mL, 2.87 mmol) in DMSO (3 mL) was stirred at 120 C for 18 h. Water and EtOAc were added. The organic phase was separated, dried over Na2SO4, concentrated in vacuo. The residue was purified by a silica gel column, which was eluted with 0-70% EtOAc in hexane to give (R)-2-(5-bromo-4-cyano-2-fluorophenylamino)-3-methoxypropanamide (52 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09359375B2 |
| Source dataset | uspto-grants-2016_06 |
| ORD ID | ord-6a1a24d380a940d1956d969732a0af14 |
| Source note | uspto-grants-2016_06 |