Sodium Iodide → 5-(5-(3-(6-chloro-2,3-dihydrospiro[indene-1,3'-pyrrolidine]-1'-yl)propylthio)-4-methyl-4H-1,2,4-triazol-3-yl)-2,4-dimethylthiazole hydrochloride

Participants

Reaction Conditions

Reaction Steps

The mixture of 6-chloro-2,3-dihydrospiro[indene-1,3′-pyrrolidine] (Prep47, 100 mg, 0.37 mmol), K2CO3 (110 mg, 0.8 mmol), sodium iodide (80 mg, 0.53 mmol), and 5-(5-(3-chloropropylthio)-4-methyl-4H-1,2,4-triazol-3-yl)-2,4-dimethylthiazole (Prep28, 80 mg, 0.28 mmol) in NMP (4 ml) was warmed to 70° C. The mixture was stirred at 70° C. overnight. The mixture diluted with water (20 ml), extracted with EA (10 ml). The organic layers were combined and washed with Sat. NaHCO3, Sat. brine and dried over anhydrous Na2SO4. The organics was evaporated under vacuum to get crude product. The crude product was purified by P-TLC (TLC analysis performed by eluting with PE/EA 1:1), then P-HPLC. The free base of the compound was then converted into the title compound (treatment with 1 eq of 1N HCl) and dried under vacuum to give the desired product as white solid (20 mg, y=11.4%).

Provenance & Evidence