HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 2-Chloro-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyridin-2-yl]amino}cyclopentyl]benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 2-Chloro-5-(trifluoromethyl)pyridine | HCID 92342 | — |
| Reactant | N-[(1S,2S)-2-Aminocyclopentyl]-2-chlorobenzamide hydrochloride | HCID 118308080 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | 2-Chloro-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyridin-2-yl]amino}cyclopentyl]benzamide | HCID 118308126 | — |
Reaction Conditions
| Temperature | 150 °C |
|---|
Reaction Steps
A solution of N-[(1S,2S)-2-aminocyclopentyl]-2-chlorobenzamide hydrochloride (Intermediate 19; 100 mg, 0.36 mmol), 2-chloro-5-(trifluoromethyl)pyridine (CAS number 52334-81-3; 79 mg, 0.44 mmol) and DIPEA (190 μl, 1.09 mmol) in dry DMSO (1.2 ml) was sealed and heated at 150° C. for 17 hours. The reaction mixture was filtered through cotton wool and purified by reverse phase preparative HPLC (eluted with acetonitrile/water containing 0.1% ammonia) to afford the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09156829B2 |
| Source dataset | uspto-grants-2015_10 |
| ORD ID | ord-58adbc4ac7d849df9f9e8d579b8d825d |
| Source note | uspto-grants-2015_10 |