HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → (R)-2-(3-bromo-4-cyanophenylamino)-3-(thiophen-2-yl)propanamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 2-Bromo-4-fluorobenzonitrile | HCID 118939 | — |
| Reactant | (R)-2-amino-3-(thiophen-2-yl)propanamide | HCID 67508269 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | (R)-2-(3-bromo-4-cyanophenylamino)-3-(thiophen-2-yl)propanamide | HCID 67508155 | 18.3% |
Reaction Steps
A solution of 2-bromo-4-fluorobenzonitrile (120 mg, 0.600 mmol), (R)-2-amino-3-(thiophen-2-yl)propanamide (93 mg, 0.547 mmol) and DIEA (0.200 mL, 1.15 mmol) in DMSO (3 mL) was stirred at 120 C for 4 d. 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 0-80% EtOAc in hexane to give (R)-2-(3-bromo-4-cyanophenylamino)-3-(thiophen-2-yl)propanamide (35 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09359375B2 |
| Source dataset | uspto-grants-2016_06 |
| ORD ID | ord-b55e2b076f43435cb384943c331a9b95 |
| Source note | uspto-grants-2016_06 |