4-Methylmorpholine → 2-[3-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]-N-[4-(1,1-dioxoisothiazolidin-2-yl)phenyl]valeramide

Participants

Role	Name	HCID	Charge
Reactant	4-Methylmorpholine	HCID 7972	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	2-[3-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]pentanoic Acid	HCID 11173437	—
Reactant	2-(4-Aminophenyl)-1lambda6,2-thiazolidine-1,1-dione	HCID 11816685	—
Reactant	HCID 178526939	HCID 178526939	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	2-[3-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]-N-[4-(1,1-dioxoisothiazolidin-2-yl)phenyl]valeramide	HCID 11408801	—

Reaction Steps

101 μl (1.00 mmol) of 4-methylmorpholine are added to a solution of 212 mg (1.00 mmol) of 2-(4-aminophenyl)isothiazolidine 1,1-dioxide, 276 mg (1.00 mmol) of 2-[3-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]-pentanoic acid, 192 mg (1.00 mmol) of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (DAPECI) and 135 mg (1.00 mmol) of hydroxybenzotriazole hydrate (HOBt) in 1 ml of DMF, and the mixture is stirred at room temperature for 24 hours. The reaction mixture is introduced into water, and the precipitate is filtered off, giving 2-[3-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]-N-[4-(1,1-dioxoisothiazolidin-2-yl)phenyl]valeramide as a colourless solid; ESI 471.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07199133B2
Source dataset	uspto-grants-2007_04
ORD ID	ord-a9ed98e55e02492cbf9274f924ef84e1
Source note	uspto-grants-2007_04