Triethylamine → 5-Chloro-1-[(3-chlorophenyl)methyl]-1,2-dihydro-2-imino-3-pyridinecarboxamide

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Reaction Steps

To a solution of 2-cyano-2-(3,4-dichloro-5-oxo-2,5-dihydrofuran-2-yl)acetamide (0.5 g) in tetrahydrofuran (10 ml) was added a solution of 3-chlorobenzylamine (0.45 g) (Table 1-1, amine 19) and triethylamine (0.32 g) in tetrahydrofuran (3 ml) under ice-cooling, and the mixture was allowed to warm to room temperature and stirred for 18 hr. The reaction mixture was concentrated, and the crystals were collected by filtration. The obtained crystals were added to a mixture of dimethylsulfoxide (5 ml)-water (5 ml), and the mixture was stirred at 80° C. for 1 hr. The reaction mixture was concentrated, the residue was purified by preparative HPLC, and the obtained fraction was treated with PL-HCO3MP (200 mg cartridge, Polymer Laboratories) to give the title compound (0.33 g).

Provenance & Evidence