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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 734754Generated: October 30, 2026

1,2-Dichloroethane → 4-[4-Chloro-3-(methyloxy)phenyl]-N-(6-fluoro-1H-indazol-5-yl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide

https://huagongshe.com/reaction/734754

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,2-DichloroethaneHCID 11—
ReactantTriethylamineHCID 8471—
Reactant6-fluoro-1H-indazol-5-amineHCID 45090504—
Reactant4-[4-Chloro-3-(methyloxy)phenyl]-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxylic acidHCID 68827256—
SolventHydrochloric AcidHCID 313—
SolventDimethylformamideHCID 6228—
SolventEthyl AcetateHCID 8857—
Product4-[4-Chloro-3-(methyloxy)phenyl]-N-(6-fluoro-1H-indazol-5-yl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamideHCID 5784528229.3%

Reaction Conditions

Temperature30 °C

Reaction Steps

6-Fluoro-1H-indazol-5-amine (102 mg, 0.676 mmol, 1.0 equiv) was combined with the product of Example 93, Step 4 (0.200 g, 0.676 mmol, 1.0 equiv), EDC (155 mg, 0.812 mmol, 1.2 equiv) and Et3N (113 μL, 0.812 mmol, 1.2 equiv) in DMF (2 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 85.0 mg (29%) of the title compound as a white solid. MS (ES+) m/e 429 [M+H]+

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07592357B2
Source datasetuspto-grants-2009_09
ORD IDord-fde6ac4e9b4c4a2996f12cdabf9324cc
Source noteuspto-grants-2009_09