(5Z)-5-[(3-cyclopentyloxy-4-methoxyphenyl)methylidene]-2-imino-1,3-thiazolidin-4-one → 6-(2-amino4-oxo4H-thiazol-5-ylidenemethyl)-[1,5]naphthyridine-3-carbonitrile

Participants

Reaction Conditions

Reaction Steps

To a mixture of pseudothiohydantoin (Aldrich, 97%, 23.2 mg, 0.20 mmol), AcONa (160 mg, 1.95 mmol), molecular sieves, and 6-formyl-[1,5]naphthyridine-3-carbonitrile (38.5 mg, 0.21 mmol) (see Example 11) in a sealed tube was added AcOH (0.3 mL). The reaction mixture was heated to 120° C. for 3.5 hrs. The reaction mixture was then cooled to r.t. and triturated with water. The solid was collected by filtration and washed with water, AcOEt and ether to give 6-(2-amino-4-oxo-4H-thiazol-5-ylidenemethyl)-[1,5]naphthyridine-3-carbonitrile as a yellowish solid (30.3 mg, 44.6%). LR-ES (+) m/e 282 (M+H).

Provenance & Evidence