6-Formyl-4-isopropoxy-[1,5]naphthyridine-3-carbonitrile → HCID 178458708, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2-(2-chloro-benzylamino)-thiazol-4-one (48.1 mg, 0.20 mmol) (prepared as described below), AcONa (160 mg, 1.95 mmol), molecular sieves, and 6-formyl-4-isopropoxy-[1,5]naphthyridine-3-carbonitrile (53.1 mg, 0.22 mmol, (see Example 1) in a sealed tube was added AcOH (0.3 mL). The reaction mixture was heated to 85-95° C. (oil bath) for 1.5 h. 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 hot MeOH (50 mL) and filtered again. The filtrate was concentrated to give a brown solid: 120.3 mg, which was purified by Biotage flash column (1%-6% MeOH in CH2Cl2) to give 6-[2-(2-chloro-benzylamino)-4-oxo-4H-thiazol-5-ylidenemethyl]-4-isopropoxy-[1,5]naphthyridine-3-carbonitrile as a yellowish solid (32.8 mg, 35.3%). HR-ES (+) m/e calcd for C23H18ClN5O2S (M+H)+ 464.0943. found 464.0943.

Provenance & Evidence