HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Pyridine → 6-Bromo-N-(2-methyl-5-(2-(4-methylpiperazin-1-yl)benzylcarbamoyl)phenyl)pyrazolo[1,5-a]pyridine-3-carboxamide
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Pyridine | HCID 1049 | — |
| Edukt | Thionyl Chloride | HCID 24386 | — |
| Edukt | 6-Bromopyrazolo(1,5-a)pyridine-3-carboxylic acid | HCID 57372319 | — |
| Edukt | 3-Amino-4-methyl-N-(2-(4-methylpiperazin-1-yl)benzyl)benzamide | HCID 86695684 | — |
| Lösungsmittel | Methanol | HCID 887 | — |
| Lösungsmittel | Ethyl Acetate | HCID 8857 | — |
| Produkt | 6-Bromo-N-(2-methyl-5-(2-(4-methylpiperazin-1-yl)benzylcarbamoyl)phenyl)pyrazolo[1,5-a]pyridine-3-carboxamide | HCID 71283253 | — |
Reaktionsschritte
A mixture comprising 6-bromopyrazolo[1,5-a]pyridine-3-carboxylic acid (commercially available) (196 mg, 0.813 mmol) and thionyl chloride (2 ml, 27.4 mmol) was heated at 60° C. for 1 hr and concentrated in vacuo. To this was added 3-amino-4-methyl-N-(2-(4-methylpiperazin-1-yl)benzyl)benzamide (step 1) (220 mg, 0.651 mmol) and pyridine (5 ml). The reaction was stirred under nitrogen at room temperature for 2 hrs. The mixture was diluted with 10% MeOH in EtOAc and washed with water, sat NaHCO3, brine and concentrated in vacuo. The crude product was purified by chromatography on silica eluting with 0-20% 2M NH3 in MeOH/DCM to afford the title compound;
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US08883819B2 |
| Quelldatensatz | uspto-grants-2014_11 |
| ORD ID | ord-597139d1a1e7458c803747dda0be57a9 |
| Quellennotiz | uspto-grants-2014_11 |