HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 2,6-Dimethoxy-N-[(1S,2S)-2-{[6-(trifluoromethyl)pyridin-2-yl]amino}cyclopentyl]benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 2-Fluoro-6-(trifluoromethyl)pyridine | HCID 2736501 | — |
| Reactant | N-((1S,2S)-2-aminocyclopentyl)-2,6-dimethoxybenzamide hydrochloride | HCID 118308159 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | 2,6-Dimethoxy-N-[(1S,2S)-2-{[6-(trifluoromethyl)pyridin-2-yl]amino}cyclopentyl]benzamide | HCID 118308116 | — |
Reaction Steps
To a microwave vial were charged N-[(1S,2S)-2-Aminocyclopentyl]-2,6-dimethoxybenzamide hydrochloride (Intermediate 5; 80 mg, 0.266 mmol) in dry NMP (1 ml). To this was then added DIPEA (138 μl, 0.798 mmol) and 2-fluoro-6-(trifluoromethyl)pyridine (CAS number 94239-04-0; 53 mg, 0.319 mmol). The reaction was subjected to microwave irradiation at 200° C. for 30 minutes and then at 250° C. for 20 minutes. The reaction mixture was directly 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-d4e59a0d7cf640eb8833a247de04eff7 |
| Source note | uspto-grants-2015_10 |