1,1'-Carbonyldiimidazole → HCID 86650046, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1,1′-carbonyldiimidazole (326.0 mg, 2.010 mmol) in anhydrous tetrahydrofuran (8 ml), a solution of N-(4-{2-[5-(sulfanylmethyl)thiophen-2-yl]ethyl}-1,3-thiazol-2-yl)acetamide (400.0 mg, 1.340 mmol) in anhydrous tetrahydrofuran (10 ml) was added dropwise at 0° C. The mixture was stirred at 0° C. for 15 min and at room temperature for 1 hr. tert-Butyl carbazate (351.4 mg, 4.021 mmol) was added, and the mixture was stirred at room temperature for 16 hr. The mixture was concentrated, and residue was added water (40 ml) and extracted 3 times with ethyl acetate. The combined organic layer was washed with ice-cooled 1M hydrochloric acid, saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 100 g, ethyl acetate:hexane=1:1) to give tert-butyl 2-({[(5-{2-[2-(acetylamino)-1,3-thiazol-4-yl]ethyl}thiophen-2-yl)methyl]sulfanyl}carbonyl)hydrazinecarboxylate (316.7 mg, 0.694 mmol, yield 51.8%) as a white solid.

Provenance & Evidence