CI.[CH3:3][C:4]1[N:9]2[N:10]=[C:11]([CH2:13][S:14][C:15]3[NH:16][N:17]=[C:18]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[N:19]=3)[N:12]=[C:8]2[CH:7]=[CH:6][CH:5]=1.[C:26](=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:3][C:4]1[N:9]2[N:10]=[C:11]([CH2:13][S:14][C:15]3[N:16]([CH3:26])[N:17]=[C:18]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[N:19]=3)[N:12]=[C:8]2[CH:7]=[CH:6][CH:5]=1Methyl iodide (142 mg, 1.00 mmol) dissolved in DMF (0.5 ml) was added to a stirred suspension of 5-Methyl-2-(5-phenyl-2H-1,2,4-triazol-3-ylsulfanylmethyl)-[1,2,4]triazolo[1,5-a]pyridine (322 mg, 1.00 mmol) and Potassium carbonate (276 mg, 2.0 mmol) in N,N-Dimethylformamide (3.5 mL) at rt, under Ar. The solution was stirred at 3 h and then quenched by adding Sat bicarbonate sol and extracting with EtOAc. The Organic phase was dried (MgSO4) and was rotovaped. The crude product was purified by HPLC. This afforded 10 mg of the title compound. LC-MS: m/z=337.1 (MH+), tR=0.63 min, Method B. 1H NMR (600 MHz, DMSO-d6): δ 7.96 (d, 2H), 7.63 (d, 1H), 7.60 (t, 1H) 7.50-7.40 (m, 3H), 7.07 (d, 1H), 4.68 (s, 2H), 2.66 (s, 3H).
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