HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Ethylpiperazine → {4-[3-(6-Amino-pyridin-3-ylethynyl)-2-ethyl-pyridin-4-yl]-2-methoxy-phenyl}-(4-ethyl-piperazin-1-yl)-methanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Ethylpiperazine | HCID 79196 | — |
| 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-[3-(6-Amino-pyridin-3-ylethynyl)-2-ethyl-pyridin-4-yl]-2-methoxy-benzoic acid | HCID 58235260 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Acetonitrile--water (1/1) | HCID 18373917 | — |
| Product | {4-[3-(6-Amino-pyridin-3-ylethynyl)-2-ethyl-pyridin-4-yl]-2-methoxy-phenyl}-(4-ethyl-piperazin-1-yl)-methanone | HCID 49801083 | — |
Reaction Steps
The title compound is synthesized according to general procedure GP5 starting from 70 mg (0.19 mmol) 4-[3-(6-Amino-pyridin-3-ylethynyl)-2-ethyl-pyridin-4-yl]-2-methoxy-benzoic acid (A-42) using 42 mg (0.38 mmoL) N-ethyl piperazine, 71 mg (0.19 mmol) HATU and 35 μL (0.21 mmol) DIPEA in 1.0 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: 85 mg (97%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09090564B2 |
| Source dataset | uspto-grants-2015_07 |
| ORD ID | ord-ddd96149f4f04e2daa38056b41524106 |
| Source note | uspto-grants-2015_07 |