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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2204743Generated: November 1, 2026

1,2-Dichloroethane → 5-Bromo-2-{[(2,4-difluorophenyl)methyl]oxy}-4-(4-morpholinylmethyl)-N-3-pyridinylbenzamide

https://huagongshe.com/reaction/2204743

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,2-DichloroethaneHCID 11—
Reactant3-AminopyridineHCID 10009—
ReactantDiisopropylethylamineHCID 81531—
ReactantHOAtHCID 181649—
Reactant5-Bromo-2-{[(2,4-difluorophenyl)methyl]oxy}-4-(4-morpholinylmethyl)benzoic acidHCID 66611303—
SolventDimethylformamideHCID 6228—
Product5-Bromo-2-{[(2,4-difluorophenyl)methyl]oxy}-4-(4-morpholinylmethyl)-N-3-pyridinylbenzamideHCID 66611954—

Reaction Steps

To a solution of 5-bromo-2-{[(2,4-difluorophenyl)methyl]oxy}-4-(4-morpholinylmethyl)benzoic acid (may be prepared as described in Description 22; 150 mg, 0.34 mmol) in N,N-dimethylformamide (4 ml) was added 3-aminopyridine (38.3 mg, 0.41 mmol), diisopropylethylamine (0.12 ml, 0.68 mmol), 1-hydroxy-7-azabenzotriazole (55.4 mg, 0.41 mmol) and EDC (98 mg, 0.51 mmol). The mixture was stirred overnight and the solvent removed in vacuo to give a residue. Purification by column chromatography (SiO2; 10% 7M NH3 in methanol/dichloromethane) yielded the title compound as a solid. 162 mg.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09365551B2
Source datasetuspto-grants-2016_06
ORD IDord-3239d45288eb480888f1128b84d9cf8d
Source noteuspto-grants-2016_06