HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Methylpiperazine → {4-[2-Ethyl-3-(6-methylamino-pyridin-3-ylethynyl)-pyridin-4-yl]-2-fluoro-phenyl}-(4-methyl-piperazin-1-yl)-methanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Methylpiperazine | HCID 53167 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | 4-[2-Ethyl-3-(6-methylamino-pyridin-3-ylethynyl)-pyridin-4-yl]-2-fluoro-benzoic acid | HCID 66770838 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Acetonitrile--water (1/1) | HCID 18373917 | — |
| Product | {4-[2-Ethyl-3-(6-methylamino-pyridin-3-ylethynyl)-pyridin-4-yl]-2-fluoro-phenyl}-(4-methyl-piperazin-1-yl)-methanone | HCID 49800790 | — |
Reaction Steps
The title compound is synthesized according to general procedure GP5 starting from 100 mg (0.27 mmol) 4-[2-Ethyl-3-(6-methylamino-pyridin-3-ylethynyl)-pyridin-4-yl]-2-fluoro-benzoic acid (A-46) using 50 μL (0.45 mmoL) N-methyl piperazine, 101 mg (0.27 mmol) HATU and 50 μL (0.29 mmol) DIPEA in 1.5 mL DMF. After completion of the reaction, the reaction mixture is filtered and the product is isolated from the obtained solution by RP-HPLC using a H2O/ACN-gradient. Yield: 70 mg (58%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09090564B2 |
| Source dataset | uspto-grants-2015_07 |
| ORD ID | ord-4d63f49be9f34b689352cfcb0ce19f22 |
| Source note | uspto-grants-2015_07 |