Pyridine → HCID 54501726, compound

Participants

Reaction Steps

In the mixture of 30 ml of pyridine and 3 ml of dimethylformamide was suspended 1.09 g of 3-propyl-6,7-dihydro-5H-thiazolo[3,2-a]pyrimidine-2-carbonylchloride hydrochloride (described in Example 13). To the suspension was added 1.02 g of N-(2-ethoxycarbonylethyl)-3,5-dichloro-aniline obtained in Reference Example 5 and 47.4 mg of 3,5-dimethylaminopyridine, followed by stirring at 70° C. for 20 hours. The reaction mixture was concentrated and to the mixture was added saturated sodium hydrogencarbonate aqueous solution. The organic layer was extracted with chloroform. The extact was washed with water and dried, followed by removing the solvent. The residue was dissolved in ethanol and to the solution was added saturated hydrogenchloride diethylether solution. The mixture was stirred at room temperature and the solvent was removed under reduced pressure. The residue was purified by column chromatography using a mixed solvent of chloroform and methanol (10:1 by volume) as an eluent. The resulting substance was crystallized from a mixed solvent of ethanol and diethylether. The formed crystals were recrystallized from a mixed solvent methanol and diethylether to obtain 109 mg of the titled compound.

Provenance & Evidence