Triethylamine → HCID 136337173, compound

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	Ethyl isothiocyanatoformate	HCID 85320	—
Reactant	3,5-Difluoroaniline	HCID 96595	—
Reactant	ethyl 1H-pyrazole-4-carboxylate	HCID 142179	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Solvent	Dichloromethane	HCID 6344	—
Product	HCID 136337173	HCID 136337173	17%

Reaction Steps

Ethyl isothiocyanatoformate (0.68 mL, 5.8 mmol) was added to a solution of 3,5-difluoroaniline (0.680 g, 5.27 mmol) and DCM (26 mL). After 3 h, triethylamine (2.20 mL, 15.8 mmol) was added to the reaction mixture, followed by ethyl pyrazole-4-carboxylate (0.812 g, 5.79 mmol), and EDCl (1.21 g, 6.32 mmol). After 1.5 h, the reaction mixture was diluted with DCM (25 mL), washed with water (3×30 mL) and with brine (50 mL), dried (MgSO4), and concentrated. The residue was purified by FCC (3-45% EtOAc/hexanes) to yield the titled compound (0.323 g, 17% yield). MS (ESI/Cl): mass calcd. for C16H16F2N4O4, 366.1; m/z found, 367.1 [M+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08937078B2
Source dataset	uspto-grants-2015_01
ORD ID	ord-2d5dc0cacb2c473dbae80cbed37de8b8
Source note	uspto-grants-2015_01