CN.[CH3:3][C:4]1[N:5]=[C:6]([NH:15][C:16]([N:18]2C=CN=[CH:19]2)=[O:17])[S:7][C:8]=1[C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=1>O.CN(C=O)C>[CH3:19][NH:18][C:16]([NH:15][C:6]1[S:7][C:8]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)=[C:4]([CH3:3])[N:5]=1)=[O:17]Methylamine (0.030 ml of a 40% w/w/solution in water, 0.351 mmol) is added to a stirred suspension of imidazole-1-carboxylic acid (4-methyl-5-pyridin-4-yl-thiazol-2-yl)-amide (18a) (0.1 g, 0.351 mmol) in DMF (3 ml). The reaction mixture is stirred at room temperature for 1 hour and then the solvent is removed in vacuo. The crude product is dissolved in THF/DMF (10:1, 3 ml) and passed through a polymer supported isocyanate resin (0.9 g, 1.1 mmol/g loading) and washed through with THF. The solution is concentrated in vacuo and the residue washed with ethyl acetate and methanol to afford the titled compound.
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