N#N.Cl[CH2:4][C:5]1[N:6]=[C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[S:8][CH:9]=1.[N+:15]([C:18]1[CH:22]=[N:21][NH:20][N:19]=1)([O-:17])=[O:16].CCN(C(C)C)C(C)C>CN(C=O)C.CC(=O)OCC.O>[N+:15]([C:18]1[CH:22]=[N:21][N:20]([CH2:4][C:5]2[N:6]=[C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[S:8][CH:9]=2)[N:19]=1)([O-:17])=[O:16]
In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of ethyl 4-(chloromethyl)thiazole-2-carboxylate (WO 2009077990 A1) (2.16 g, 10.5 mmol) in DMF (15.0 mL) was added to a solution of 4-nitro-2H-[1,2,3]triazole (T. E. Eagles et al. Organic preparations and procedures 2 (2), 117-119, 1970; P. N. Neuman J. Heterocycl. Chem. 8, 51-56, 1971) (8.0 g of a 10% solution in DMF, 7.01 mmol) in DMF (15.0 mL) pre-treated for 30 min with DIPEA (1.82 mL, 2.33 mmol) and the reaction mixture was stirred overnight at 50° C. Water (50 mL), followed by EA (50 mL) was added. The layers were separated and the aq. layer was washed with water (50 mL), dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (60:40 hept-EA)) gave the title compound as a yellow oil. TLC: rf (7:3 hept-EA)=0.36. LC-MS-conditions 07: tR=0.76 min, [M+H]+=284.28.
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