1,2-Dichloroethane → HCID 178487581, compound

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 178434299	HCID 178434299	—
Solvent	Hydrochloric Acid	HCID 313	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	HCID 178487581	HCID 178487581	62%

Reaction Conditions

Temperature	30 °C

Reaction Steps

3-Methyl-1H-indazol-5-amine (87 mg, 0.592 mmol, 1.0 equiv) was combined with the product of Example 93, Step 4 (175 mg, 0.592 mmol, 1.0 equiv), EDC (134 mg, 0.710 mmol, 1.2 equiv) and Et3N (99 μL, 0.710 mmol, 1.2 equiv) in DMF (1.75 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 155 mg (62%) of the title compound as a white solid. MS (ES+) m/e 425 [M+H]+

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07592357B2
Source dataset	uspto-grants-2009_09
ORD ID	ord-27f59b013ecc4c5bada7fa8387897ed6
Source note	uspto-grants-2009_09