HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl Acetate → (R)-2-(6-chloro-5-cyano-3-fluoropyridin-2-ylamino)butanamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 2,6-Dichloro-5-fluoro-3-pyridinecarbonitrile | HCID 2733849 | — |
| Reactant | (2R)-2-aminobutanamide hydrochloride | HCID 16218339 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | (R)-2-(6-chloro-5-cyano-3-fluoropyridin-2-ylamino)butanamide | HCID 86666160 | 98.2% |
Reaction Steps
To the mixture of (R)-(−)-2-aminobutanamide hydrochloride (1.00 g, 7.2 mmol) and 2,6-dichloro-5-fluoro-3-pyridinecarbonitrile (0.92 g, 4.8 mmol) in 40 mL NMP added DIEA (2.5 mL, 14.4 mmol). The mixture was then sent to 100° C. for stirring for 1 h. The mixture was cooled to RT, and to it was poured 300 mL EtOAc. The mixture was washed with brine four times. The organic phase was dried, concentrated and purified using silica flash column (70% EtOAc-30% DCM) to isolate (R)-2-(6-chloro-5-cyano-3-fluoropyridin-2-ylamino)butanamide (1.21 g, 98% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08846928B2 |
| Source dataset | uspto-grants-2014_09 |
| ORD ID | ord-ebeeb81edffd47e99c139fc55dd2bd37 |
| Source note | uspto-grants-2014_09 |