tert-Butyl bromoacetate → HCID 66669275, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 4-(2-(3-aminophenyl)-5-oxo-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-7-yl)piperazine-1-carboxylate (50 mg, 0.117 mmol, 1.0 equiv) in 1.0 mL tetrahydrofuran is added dropwise a solution of tert-butyl bromoacetate (0.069 mL, 0.467 mmol, 4.0 equiv) in 0.5 mL tetrahydrofuran and a solution of N,N-diisopropylethylamine (0.082 mL, 0.467 mmol, 4.0 equiv) in 0.5 mL tetrahydrofuran. The mixture is heated in a microwave reactor for 30 min at 120° C. Upon completion, the mixture is taken up in water and EtOAc. The layers are separated and the aqueous layer is back-extracted with EtOAc. The combined organic extracts are washed with water and brine, and concentrated in vacuo to give crude tert-butyl 4-(2-(3-(2-tert-butoxy-2-oxoethylamino)phenyl)-5-oxo-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-7-yl)piperazine-1-carboxylate as a yellow solid. The residue is then taken on crude to the next reaction, which followed the same deprotection procedure as above to give 2-(3-(5-oxo-7-(piperazin-1-yl)-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-2-yl)phenylamino)acetic acid (18 mg, 40%) as a tan solid.

Provenance & Evidence