Sodium Acetate → 6-[2-Amino-4-oxo-4h-thiazol-(5z)-ylidenemethyl]-4-ethoxy-quinoline-3-carbonitrile

Participants

Role	Name	HCID	Charge
Reactant	Sodium Acetate	HCID 517045	—
Reactant	4-Ethoxy-6-formyl-quinoline-3-carbonitrile	HCID 58585818	—
Reactant	(5Z)-5-[(3-cyclopentyloxy-4-methoxyphenyl)methylidene]-2-imino-1,3-thiazolidin-4-one	HCID 137629131	—
Solvent	Acetic Acid	HCID 176	—
Product	6-[2-Amino-4-oxo-4h-thiazol-(5z)-ylidenemethyl]-4-ethoxy-quinoline-3-carbonitrile	HCID 11594988	47%

Reaction Conditions

Temperature	110 °C

Reaction Steps

To the suspension of 4-ethoxy-6-formyl-quinoline-3-carbonitrile (example 14e) (45 mg, 0.2 mmol) and pseudothiohydantoin (35 mg, 0.3 mmol) in acetic acid (1 mL) was added sodium acetate (66 mg, 0.8 mol). The mixture was heated to 110° C. for 4 h. After cooling to room temperature, the ice water was added. The solid was collected by filtration, washed with water and dried. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 0%-5% methanol in methylene chloride in 30 min) afforded 6-[2-amino-4-oxo-4H-thiazol-(5Z)-ylidenemethyl]-4-ethoxy-quinoline-3-carbonitrile (30 mg, 47%) as a light yellow solid: LC-MS m/e 445 (MH+).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07250515B2
Source dataset	uspto-grants-2007_07
ORD ID	ord-95fb67b45b9a4bd98586059bc6fc1bb4
Source note	uspto-grants-2007_07