[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([CH2:12][C:13](=O)[CH3:14])=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.[NH2:16][C:17]([NH2:19])=[S:18].II.CCO>N1C=CC=CC=1.CCOC(C)=O>[CH3:14][C:13]1[N:16]=[C:17]([NH2:19])[S:18][C:12]=1[C:9]1[CH:10]=[CH:11][C:6]([N:1]2[CH:5]=[CH:4][CH:3]=[N:2]2)=[CH:7][CH:8]=1A solution of 1-(4-pyrazol-1-yl-phenyl)-propan-2-one (6.9 g, 34.46 mmol) in pyridine (30 ml) is treated with thiourea (2.6 g, 34.46 mmol) followed by iodine (8.7 g, 34.46 mmol) and heated to 80° C. After 8 hours, the reaction mixture is allowed to cool to room temperature and the resulting suspension is filtered and washed with EtOAc. The filtrate is concentrated in vacuo to afford an oil. The oil is dissolved in EtOAc (200 ml) and washed with NaHCO3 (2×100 ml), brine (100 ml), dried (MgSO4) and concentrated in vacuo to afford a sticky solid. EtOH is added to the crude residue and the resulting precipitate is filtered and dried to afford the title compound (MH+ 257.29).
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