Benzoic Acid → 2-[(5-methylpyrazin-2-yl)methylamino]-5-(1,5-naphthyridin-2-ylmethylidene)-1,3-thiazol-4-one

Participants

Reaction Conditions

Reaction Steps

To a suspension of 2-[(5-methyl-pyrazin-2-ylmethyl)-amino]-thiazol-4-one (35.6 mg, 0.16 mmol), and 1,5-naphthyridine-6-carboxaldehyde (31.6 mg, 0.2 mmol) in toluene (1 mL) in a microwave tube were added benzoic acid (2.0 mg, 0.02 mmol) and piperidine (1.7 uM, 0.02 mmol). The reaction mixture was heated to 130° C. with microwave for 10 min., then cooled to r.t. and diluted with toluene. The solid was collected by filtration and washed with toluene, MeOH and ether to give 2-[(5-methyl-pyrazin-2-ylmethyl)-amino]-5-[1,5] naphthyridin-2-ylmethylene-thiazol-4-one as a brown solid (10.6 mg, 18.3%). HR-ES (+) m/e calcd. for C18H14N6OS: (M+H)+ 363.1023. Found: 363.1022.

Provenance & Evidence