Benzoyl isothiocyanate → HCID 24855566, compound

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Reaction Steps

Benzoyl isothiocyanate (0.62 mL, 4.64 mmol) was added, dropwise, to a solution of 4-{[(3,5-dimethylisoxazol-4-yl)methyl]amino}-1H-imidazole-5-carboxamide (0.91 g, 3.86 mmol, obtained from Example 21(a)) in acetone (20 mL). After stirring o.n., the solvent was evaporated in vacuo and the residue triturated with dichloromethane. The solid was removed by filtration and the filtrate was concentrated in vacuo. A solution of ammonia in methanol (7 N, 20 mL) was added to the resulting residue and this solution was transferred to a sealable tube. The vessel was sealed and placed in an 80° C. oil bath for 3 h. After cooling to r.t., the solution was concentrated in vacuo. The product was purified by recrystallization from DMSO/water, filtered and triturated sequentially with water, methanol and dichloromethane, providing the title compound (0.10 g, 10% yield) as a solid.

Provenance & Evidence