HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Triethylamine → 8-amino-5-bromo-N-[(1S,2S)-2-hydroxycyclohexyl]-1-methyl-1,2,3,4-tetrahydroquinoline-7-carboxamide
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Triethylamine | HCID 8471 | — |
| Edukt | Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate | HCID 151348 | — |
| Edukt | (1S,2S)-2-aminocyclohexanol | HCID 7057408 | — |
| Edukt | 8-Amino-5-bromo-1-methyl-1,2,3,4-tetrahydroquinoline-7-carboxylic acid | HCID 89188577 | — |
| Lösungsmittel | Dimethylformamide | HCID 6228 | — |
| Produkt | 8-amino-5-bromo-N-[(1S,2S)-2-hydroxycyclohexyl]-1-methyl-1,2,3,4-tetrahydroquinoline-7-carboxamide | HCID 89216070 | — |
Reaktionsschritte
To a solution of 8-amino-5-bromo-1-methyl-1,2,3,4-tetrahydroquinoline-7-carboxylic acid (600 mg, 2.10 mmol) in DMF (7 mL) at rt was added (1S,2S)-2-aminocyclohexanol (242 mg, 2.10 mmol), BOP (1.16 g, 2.63 mmol), and Et3N (0.59 mL, 4.21 mmol). The mixture was stirred at rt for 2 h. The resulting solution was quenched with 10% aqueous NaHCO3 and extracted with ethyl acetate. The combined extracts were washed with water and brine, dried (Na2SO4), and concentrated to afford 8-amino-5-bromo-N-[(1S,2S)-2-hydroxycyclohexyl]-1-methyl-1,2,3,4-tetrahydroquinoline-7-carboxamide in pure form.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US09284312B2 |
| Quelldatensatz | uspto-grants-2016_03 |
| ORD ID | ord-40109f755ad14a5fb00c93bb855a2006 |
| Quellennotiz | uspto-grants-2016_03 |