Trifluoroacetic acid → RUC-4

Participants

Reaction Steps

To a solution of tert-butyl 4-(2-(5-(2-(tert-butoxycarbonylamino)acetamido)pyridin-3-yl)-5-oxo-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-7-yl)piperazine-1-carboxylate (20 mg, 0.034 mmol) in DCM (2 ml) is added TFA (0.5 ml). The mixture is stirred for 2 h, concentrated in vacuo and the residue is directly purified by preparative HPLC to give the desired product 2-Amino-N-(5-(5-oxo-7-(piperazin-1-yl)-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-2-yl)pyridin-3-yl)acetamide: 1H NMR (400 MHz, DMSO-d6) δ 11.11 (s, 1H), 9.10-8.90 (br.s., 2H), 8.94 (d, J=2.0 Hz, 1H), 8.83 (d, J=2.0 Hz, 1H), 8.67 (t, J=2.0 Hz, 1H), 8.35-8.15 (br.s., 3H), 5.62 (s, 1H), 3.89 (s, 2H), 3.85 (t, J=5.2 Hz, 4H), 3.20 (t, J=5.2 Hz, 4H); LC/MS: tR=1.908 min; HRMS: m/z (M+H+)=387.1344 (Calculated for C16H19N8O2S=387.1352).

Provenance & Evidence