HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → HCID 118308181, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 2-Chloro-5-(trifluoromethyl)pyridine | HCID 92342 | — |
| Reactant | HCID 118308235 | HCID 118308235 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 118308181 | HCID 118308181 | — |
Reaction Steps
To a solution of N-[(1S,2S)-2-aminocyclopentyl]-N-cyclobutyl-2,6-dimethoxybenzamide hydrochloride (Intermediate 18; 200 mg, 0.56 mmol) in dry DMSO (1.9 ml) was added 2-chloro-5-(trifluoromethyl)pyridine (CAS number 52334-81-3; 153 mg, 0.85 mmol) and DIPEA (295 μl, 1.69 mmol). The reaction subjected to microwave irradiation at 150° C. for 2 hours and then was partitioned between ethyl acetate and water. The organics were washed with water and brine, dried over magnesium sulfate and concentrated in vacuo. This was then purified using column chromatography (silica, 0-100% ethyl acetate/petrol) and then further 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-98e44841b99b4060808c30a9e863d897 |
| Source note | uspto-grants-2015_10 |