Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Trifluoroacetic acid | HCID 6422 | — |
| Edukt | Diisopropylethylamine | HCID 81531 | — |
| Edukt | Sodium Bicarbonate | HCID 516892 | — |
| Edukt | PyBOP | HCID 2724699 | — |
| Edukt | 5-Cyanopyridine-2-carboxylic acid | HCID 12400734 | — |
| Edukt | tert-butyl (+/-)-[(4aR*,8aS*)-8a-(6-amino-2,2-difluorobenzo[1,3]dioxol-4-yl)-4,4a,5,6,8,8a-hexahydro-7-oxa-3-thia-1-azanaphthalen-2-yl]carbamate | HCID 59281180 | — |
| Lösungsmittel | Water | HCID 962 | — |
| Lösungsmittel | Dichloromethane | HCID 6344 | — |
| Produkt | HCID 45279959 | HCID 45279959 | — |
Reaktionsschritte
5-Cyanopyridine-2-carboxylic acid (4.0 mg), diisopropylethylamine (11.5 μl) and PyBOP (17.6 mg) were added to a solution of tert-butyl (±)-[(4aR*,8aS*)-8a-(6-amino-2,2-difluorobenzo[1,3]dioxol-4-yl)-4,4a,5,6,8,8a-hexahydro-7-oxa-3-thia-1-azanaphthalen-2-yl]carbamate (10 mg) in dichloromethane (2.0 ml) in an ice bath. The mixture was heated to room temperature and stirred for four hours. The solvent was evaporated under reduced pressure and the residue was purified by NH-pTLC to obtain an intermediate. The resulting intermediate was dissolved in dichloromethane (3.0 ml) and TFA (1.0 ml) was added. After stirring at room temperature for four hours, the reaction solution was diluted with water and neutralized with a sodium bicarbonate solution. The aqueous layer was extracted with dichloromethane, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by NH-pTLC to obtain the title compound.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US08198269B2 |
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| Quelldatensatz | uspto-grants-2012_06 |
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| ORD ID | ord-39bc75924af84a62a8b718f43cc4731a |
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| Quellennotiz | uspto-grants-2012_06 |
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