HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,2-Dichloroethane → {4-[3-(6-Amino-pyridin-3-ylethynyl)-2-ethyl-pyridin-4-yl]-2-chloro-phenyl}-(4-methyl-piperazin-1-yl)-methanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,2-Dichloroethane | HCID 11 | — |
| Reactant | 1-Methylpiperazine | HCID 53167 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 4-[3-(6-Amino-pyridin-3-ylethynyl)-2-ethyl-pyridin-4-yl]-2-chloro-benzoic acid | HCID 58235287 | — |
| 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-chloro-phenyl}-(4-methyl-piperazin-1-yl)-methanone | HCID 49800789 | — |
Reaction Steps
The title compound is synthesized according to general procedure GP5 starting from 100 mg (0.27 mmol) 4-[3-(6-Amino-pyridin-3-ylethynyl)-2-ethyl-pyridin-4-yl]-2-chloro-benzoic acid (A-40) using 40 mg (0.40 mmoL) N-methyl piperazine, 102 mg (0.53 mmol) EDC, 72 mg (0.53 mmol) HOBt and 68 mg (0.53 mmol) DIPEA in 1.2 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: 66 mg (54%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09090564B2 |
| Source dataset | uspto-grants-2015_07 |
| ORD ID | ord-f2a4ef04d7024db5a0b42121af6d4967 |
| Source note | uspto-grants-2015_07 |