Sodium Bicarbonate → (+)-1-{[6-Chloro-2-(methoxymethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl}-4-(3,3,3-trifluoropropyl)pyrrolidin-2-one

Participants

Reaction Conditions

Reaction Steps

To a hot solution (80° C.) of AlCl3 (0.842 g, 6.3 mmol, 1 eq) and 6-chloro-2-(methoxy-methyl)imidazo[2,1-b][1,3,4]thiadiazole a35 (0.643 g, 3.156 mmol, 1 eq) in dioxane (35 ml) is added a solution of 1-(chloromethyl)-4-(3,3,3-trifluoropropyl)pyrrolidin-2-one a20 (1.2 g) in dioxane (5 ml). The reaction mixture is heated at 85° C. for 3 days. After cooling and hydrolysis by a saturated solution of NaHCO3 (40 ml), the crude reaction mixture is extracted by ethyl acetate (3×25 ml). The cumulated organic layers are dried over MgSO4, filtered and condensed under reduced pressure. The residue is purified by chromatography over silicagel (eluent CH2Cl2/MeOH/NH4OH 99:1:0.1) and recrystallized from diisopropyl ether to afford pure (+)-1-{[6-chloro-2-(methoxymethyl)-imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl}-4-(3,3,3-trifluoropropyl)pyrrolidin-2-one 27.

Provenance & Evidence