6-Formyl-4-isopropoxy-[1,5]naphthyridine-3-carbonitrile → HCID 178458709, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2-(2-chloro-4-fluoro-benzylamino)-thiazol-4-one (41.4 mg, 0.16 mmol) (prepared as described below), AcONa (160 mg, 1.95 mmol), and 6-formyl-4-isopropoxy-[1,5]naphthyridine-3-carbonitrile (50.2 mg, 0.21 mmol) (see Example 1) in a sealed tube was added AcOH (0.3 mL). The reaction mixture was heated to 80° C. (oil bath) for 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. The solid was then suspended in AcOEt, re-filtered through a paper filter to give 6-[2-(2-chloro-4-fluoro-benzylamino)-4-oxo-4H-thiazol-5-ylidenemethyl]-4-isopropoxy-[1,5]naphthyridine-3-carbonitrile as a light brown solid (19.2 mg, 24.9%). HR-ES (+) m/e calcd for C23H17FClN5O2S (M+H)+ 482.0849. found 482.0848.

Provenance & Evidence