Pyridine → HCID 19978087, compound

Participants

Reaction Conditions

Reaction Steps

In the mixture of 50 ml of pyridine and 5 ml of dimethylformamide was suspended 0.95 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 1.0 g of 4-(5-ethoxycarbonylpentylthio) aniline prepared in a similar manner as described in Reference Example 7 and added 43.4 mg of dimethylaminopyridine, followed by stirring at 70° C. for 16 hours. The reaction mixture was concentrated and to the concentrate was added saturated sodium hydrogencarbonate aqueous solution. The mixture was extracted with chloroform. The extract was washed with saturated sodium chloride aqueous solution and dried over anhydrous potassium carbonate. The solvent was removed under reduced pressure. The residue was dissolved in ethanol. To the mixture was added saturated hydrogenchloride diethylether solution and stirred at room temperature, following by removing the solvent under reduced pressure. The residue was purified by silica gel column chromatography (silica gel:100 g) using a mixed solvent of chloroform and methanol (10:1 by volume) as an eluent. To the resulting substance was added saturated hydrogenchloride diethylether solution. The solvent was removed under reduced pressure. The residue was recrystallized from methanol-diethylether to obtain 632 mg of the titled compound.

Provenance & Evidence