HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 1-(6-Chloro-5-cyano-3-fluoropyridin-2-ylamino)cyclopentanecarboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 2,6-Dichloro-5-fluoro-3-pyridinecarbonitrile | HCID 2733849 | — |
| Reactant | 1-Aminocyclopentane-1-carboxamide hydrochloride | HCID 54593188 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 1-(6-Chloro-5-cyano-3-fluoropyridin-2-ylamino)cyclopentanecarboxamide | HCID 86666167 | 49% |
Reaction Steps
A solution of 2,6-dichloro-3-cyano-5-fluoropyridine (250 mg, 1.30 mmol), 1-aminocyclopentanecarboxamide hydrochloride (214 mg, 1.30 mmol) and DIEA (0.650 mL, 3.73 mmol) in DMSO (3 mL) was stirred at 95 C for 4 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, eluted with 50-100% EtOAc in hexane to give 1-(6-chloro-5-cyano-3-fluoropyridin-2-ylamino)cyclopentanecarboxamide (180 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09359375B2 |
| Source dataset | uspto-grants-2016_06 |
| ORD ID | ord-9b1b06fdd12d443bb23d15c821cf8101 |
| Source note | uspto-grants-2016_06 |