Trifluoroacetic acid → HCID 178420911, compound

Participants

Reaction Steps

TFA (1.0 mL, 13 mmol) was added to a stirred solution of tert-butyl (2S)-2-(4-(5′-(2-((2S)-1-(tert-butoxycarbonyl)-2-pyrrolidinyl)-1H-imidazol-5-yl)-2,2′-bi-1,3-thiazol-5-yl)-1H-imidazol-2-yl)-1-pyrrolidinecarboxylate (55 mg, 0.086 mmol) in dichloromethane (5 mL) and the reaction mixture was stirred at room temperature for 2 h. The volatiles were removed under vacuum and the crude product was purified by preparative HPLC (Waters Sunfire C18 column 30×150 mm 5 u, eluted with a gradient of 10 to 100% acetonitrile/water/0.1% TFA). Fractions containing the desired product were filtered through a Strata XC MCX cartridge. The cartridge was washed with methanol and the compound was released from the cartridge by washing the column with a 2M ammonia in methanol solution. The filtrate was evaporated under reduced pressure to yield 5,5′-bis(2-((2S)-2-pyrrolidinyl)-1H-imidazol-4-yl)-2,2′-bi-1,3-thiazole (39 mg, 0.085 mmol, 99% yield) as an orange solid.

Provenance & Evidence