1,2-Dichloroethane → HCID 66668008, compound

Participants

Reaction Steps

Crude tert-butyl 4-(2-(3-aminophenyl)-5-oxo-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-7-yl)piperazine-1-carboxylate (60 mg, 0.140 mmol) is taken up in DMF (1.5 mL) and to it is added the Boc-glycine (37 mg, 0.210 mmol) then EDC (40.3 mg, 0.210 mmol). The mixture is stirred at room temperature for 24 hours and the reaction mixture is then taken up in water and ethyl acetate. The layers are separated and the aqueous layer is extracted with ethyl acetate. The combined organic extracts are then washed with water twice, then brine, dried over MgSO4, and concentrated in vacuo to give a yellow solid which is purified via column chromatography with 2-7% MeOH/DCM gradient to give tert-butyl 4-(2-(3-(2-(tert-butoxycarbonylamino)acetamido)phenyl)-5-oxo-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-7-yl)piperazine-1-carboxylate (crude material confirmed by LCMS analysis). The residue is then taken up in 2 mL of dichloromethane and trifluoroacetic acid (1 ml, 13.0 mmol) is added and the mixture is stirred for 18 hours. The solution is then concentrated in vacuo and washed with dichloroethane to give a crude yellow solid that is dissolved in methanol and purified by preparative HPLC to give 2-amino-N-(3-(5-oxo-7-(piperazin-1-yl)-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-2-yl)phenyl)acetamide (40 mg, 49%) as a tan solid after HPLC purification.

Provenance & Evidence