HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Dimethylformamide → 2-bromo-6-{[(3R)-3-methoxypyrrolidin-1-yl]carbonyl}pyridine
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Dimethylformamide | HCID 6228 | — |
| Edukt | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Edukt | Diisopropylethylamine | HCID 81531 | — |
| Edukt | 3-Bromopyridine-2-carboxylic Acid | HCID 2050129 | — |
| Edukt | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Edukt | 5,6,7,8-Tetrahydroimidazo(1,2-a)pyrazine | HCID 13247046 | — |
| Lösungsmittel | Dichloromethane | HCID 6344 | — |
| Produkt | 2-bromo-6-{[(3R)-3-methoxypyrrolidin-1-yl]carbonyl}pyridine | HCID 59525609 | — |
Reaktionsschritte
A solution of HOBt (148 mg, 0.97 mmol), DIEA (130 μL, 0.74 mmol), HATU (367 mg, 0.97 mmol), bromopyridine-2-carboxylic acid (150 mg, 0.74 mmol) and 5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine (91 mg, 0.74 mmol) in DMF (2.5 mL) was stirred overnight at 65° C. Upon completion, Si-carbonate (2.8 g, 2.23 mmol) and DCM (3 mL) were added and the mixture was shaken overnight at room temperature. The resulting mixture was then filtered, washed with DCM, concentrated in vacuo and purified by reverse phase HPLC (acetonitrile/water+formic acid modifier) to afford the title compound.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US08367706B2 |
| Quelldatensatz | uspto-grants-2013_02 |
| ORD ID | ord-ef6d136ec9034e4880c918885b1dd270 |
| Quellennotiz | uspto-grants-2013_02 |