HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
1,2-Dichloroethane → 2-Methoxy-5-methyl-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]benzamide
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | 1,2-Dichloroethane | HCID 11 | — |
| Edukt | Triethylamine | HCID 8471 | — |
| Edukt | HOAt | HCID 181649 | — |
| Edukt | 2-Methoxy-5-methylbenzoic acid | HCID 520167 | — |
| Edukt | (1S,2S)-1-N-[5-(Trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine hydrochloride | HCID 118308118 | — |
| Lösungsmittel | Dichloromethane | HCID 6344 | — |
| Produkt | 2-Methoxy-5-methyl-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]benzamide | HCID 118308274 | — |
Reaktionsschritte
A solution of (1S,2S)-1-N-[5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine hydrochloride (Intermediate 14, 75 mg, 0.27 mmol), 2-methoxy-5-methylbenzoic acid (CAS number 25045-36-7; 53 mg, 0.32 mmol), 3H-[1,2,3]triazolo[4,5-b]pyridin-3-ol (61 mg, 0.40 mmol), EDC (76 mg, 0.40 mmol) and triethylamine (111 μl, 0.80 mmol) in dry DCM (1 ml) was stirred at room temperature for 24 hours. The reaction mixture was partitioned between DCM (3 ml) and water (2 ml), filtered through a hydrophobic frit and concentrated in vacuo. The resulting residue was purified by reverse phase preparative HPLC (eluted with acetonitrile/water containing 0.1% ammonia) to afford the title compound.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US09156829B2 |
| Quelldatensatz | uspto-grants-2015_10 |
| ORD ID | ord-9525528273c5439c894b3cbfda62fb66 |
| Quellennotiz | uspto-grants-2015_10 |