Cl.NO.C([N:7](CC)C(C)C)(C)C.[Br:13][C:14]1[C:15]([NH:20][C:21]([NH:23]C(=O)OCC)=S)=[N:16][CH:17]=[CH:18][CH:19]=1>CO.C(O)C>[Br:13][C:14]1[C:15]2[N:16]([N:7]=[C:21]([NH2:23])[N:20]=2)[CH:17]=[CH:18][CH:19]=1To a solution of hydroxylamine hydrochloride (0.10 kg, 1.4 mol, 5.0 equiv) and N,N-diisopropylethylamine (112 g, 0.867 mol, 3.00 eq) in 1:1 methanol/ethanol (1.5 L) was added ethyl [(3-bromopyridin-2-yl)carbamothioyl]carbamate (88 g, 0.29 mmol, 1 equiv) in one portion at room temperature. After 2 h, the reaction mixture was warmed to 60° C. for overnight. The reaction mixture was concentrated in vacuo, and water was added to the resulting residue. The solids were filtered and rinsed sequentially with 4:1 methanol/diethyl ether and diethyl ether to provide product as an off-white solid (25 g, 40%). LCMS (ESI) m/z: 212.8; 1H NMR (400 MHz, DMSO-d6) δ: 8.55 (m 1H), 7.70 (m, 1H), 6.75 (m, 1H), 6.20 (br s, 2H).
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