HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 734753Generated: October 30, 2026
1,2-Dichloroethane → 4-[4-Chloro-3-(methyloxy)phenyl]-N-(3-ethyl-1H-indazol-5-yl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide
https://huagongshe.com/reaction/734753
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 1,2-Dichloroethane | HCID 11 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 4-[4-Chloro-3-(methyloxy)phenyl]-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxylic acid | HCID 68827256 | — |
| Reactant | HCID 178438005 | HCID 178438005 | — |
| Solvent | Hydrochloric Acid | HCID 313 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 4-[4-Chloro-3-(methyloxy)phenyl]-N-(3-ethyl-1H-indazol-5-yl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide | HCID 178438011 | 50% |
Reaction Steps
3-Ethyl-1H-indazol-5-amine (218 mg, 1.35 mmol, 1.00 equiv) was combined with the product from Example 93, Step 4 (0.400 g, 1.35 mmol, 1.00 equiv), EDC (0.310 g, 1.62 mmol, 1.2 equiv) and Et3N (226 μL, 1.62 mmol, 1.20 equiv) in DMF (4 mL) and stirred at 30° C. for 18 hours. The reaction mixture was diluted with EtOAc and 1N HCl. The phases were separated, and the organic phase was washed twice with 1N HCl, once with satd. NaHCO3, and once with satd. NaCl. Solid precipitated out of the organic phase and was filtered and triturated with ether to provide 295 mg (50%) of the title compound as a white solid. MS (ES+) m/e 439 [M+H]+
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07592357B2 |
|---|
| Source dataset | uspto-grants-2009_09 |
|---|
| ORD ID | ord-ae0e4c085be44ad5a6364f88fc28ea08 |
|---|
| Source note | uspto-grants-2009_09 |
|---|