Diisopropylethylamine → (E)-2-Bromo-N'-methyl-N'-propionyl-4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-en-1-yl)benzohydrazide

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	N-methylpropionohydrazide	HCID 542680	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	(E)-2-bromo-4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-enyl)benzoic acid	HCID 86722549	—
Catalyst	4-(Dimethylamino)pyridine	HCID 14284	—
Solvent	1,2-Dichloroethane	HCID 11	—
Solvent	Water	HCID 962	—
Product	(E)-2-Bromo-N'-methyl-N'-propionyl-4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-en-1-yl)benzohydrazide	HCID 86722548	—

Reaction Steps

To a stirred solution of (E)-2-bromo-4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl) but-1-enyl) benzoic acid (200 mg, 0.41 mmol) in DCE (15 mL) was added N-methylpropionohydrazide (WO 2009110510) (50 mg, 0.49 mmol), DMAP (55 mg, 0.45 mmol), EDC.HCl (60 mg, 0.41 mmol) and DIPEA (0.20 mL, 1.1 mmol). The reaction mixture was stirred at 25° C. for 12 h, —diluted with water and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated under reduced pressure. Purification by flash column chromatography (SiO2, 100-200 mesh) eluting with 30% EtOAc in hexane afforded the title compound as an off white solid (86 mg, 34%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09211281B2
Source dataset	uspto-grants-2015_12
ORD ID	ord-d9d6d7a61215429a99c52141a3ea65e8
Source note	uspto-grants-2015_12