HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Tetrahydrofuran → 6,6-Dimethyl-8-(1-oxetan-3-yl-piperidin-4-ylmethoxy)-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Tetrahydrofuran | HCID 8028 | — |
| Edukt | Sodium cyanoborohydride | HCID 5003444 | — |
| Edukt | 3-Oxetanone | HCID 15024254 | — |
| Edukt | 6,6-Dimethyl-11-oxo-8-(piperidin-4-ylmethoxy)-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile hydrochloric acid salt | HCID 66834300 | — |
| Lösungsmittel | Acetic Acid | HCID 176 | — |
| Lösungsmittel | Methanol | HCID 887 | — |
| Lösungsmittel | Water | HCID 962 | — |
| Produkt | 6,6-Dimethyl-8-(1-oxetan-3-yl-piperidin-4-ylmethoxy)-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile | HCID 66834438 | 43,9% |
Reaktionsschritte
6,6-Dimethyl-11-oxo-8-(piperidin-4-ylmethoxy)-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile hydrochloric acid salt (Compound A7-25, 30 mg, 0.075 mmol) and oxetan-3-one (38 mg, 7 eq.) were dissolved in acetic acid (0.2 ml), THF (1 ml) and methanol (1 ml), added with sodium cyanoborohydride (33 mg, 7 eq.) at room temperature, and stirred overnight. The reaction solution was added with water, and then extracted with ethyl acetate. The solution was dried over sodium sulfate and the solvent was removed under vacuum and the resulting residues were purified by preparative TLC (chloroform: 2 N ammonia methanol=9:1) to obtain the target compound (15 mg).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US09440922B2 |
| Quelldatensatz | uspto-grants-2016_09 |
| ORD ID | ord-b18223b5a281405fb046a292826eac0a |
| Quellennotiz | uspto-grants-2016_09 |