[NH2:1][C:2]1[CH:3]=[C:4]([C:9]2[S:31][C:12]3=[N:13][C:14]([N:18]4[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]4)=[CH:15][C:16](=[O:17])[N:11]3[N:10]=2)[CH:5]=[C:6]([Br:8])[CH:7]=1.[NH:32](C(OC(C)(C)C)=O)[CH2:33][C:34](O)=[O:35].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[NH2:32][CH2:33][C:34]([NH:1][C:2]1[CH:3]=[C:4]([C:9]2[S:31][C:12]3=[N:13][C:14]([N:18]4[CH2:19][CH2:20][NH:21][CH2:22][CH2:23]4)=[CH:15][C:16](=[O:17])[N:11]3[N:10]=2)[CH:5]=[C:6]([Br:8])[CH:7]=1)=[O:35]To a solution of tert-butyl 4-(2-(3-amino-5-bromophenyl)-5-oxo-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-7-yl)piperazine-1-carboxylate (30.0 mg, 0.059 mmol) in DMF (2 ml) are added Boc-Gly-OH (20.7 mg, 0.118 mmol), HATU (45.0 mg, 0.118 mmol) and i−Pr2NEt (31 μl, 0.177 mmol). The mixture is stirred at room temperature for 2 h. EtOAc (10 ml) is added and the solution is washed with H2O and brine. The organic layer is dried over Na2SO4. After removing EtOAc, the residue is purified by Biotage column chromatography (MeOH/DCM: 1/100 to 1/20 gradient) to give the desired product (33 mg, 84%).
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