Br[C:2]1[S:6][C:5]([NH:7][C:8]2[CH:13]=[C:12]([CH2:14][O:15][Si](C(C)(C)C)(C)C)[CH:11]=[CH:10][N:9]=2)=[N:4][CH:3]=1.[SH:23][C:24]1[CH:29]=[CH:28][N:27]=[C:26]([C:30]([O:32]C)=[O:31])[CH:25]=1.C[O-].[Na+].[OH-].[Na+].Cl>CO.CN(C)C=O>[OH:15][CH2:14][C:12]1[CH:11]=[CH:10][N:9]=[C:8]([NH:7][C:5]2[S:6][C:2]([S:23][C:24]3[CH:29]=[CH:28][N:27]=[C:26]([C:30]([OH:32])=[O:31])[CH:25]=3)=[CH:3][N:4]=2)[CH:13]=1
A solution of 5-bromo-N-(4-((tert-butyldimethylsilyloxy)methyl)pyridine-2-yl)thiazol-2-amine (0.907 g, 2.27 mmol, described in the synthesis of bromides or thioisocyanates, Example A) in methanol (15 mL) was treated with the previously prepared solution of methyl 4-mercaptopicolinate in N,N-dimethylformamide and sodium methoxide (1.47 mL, 25% in MeOH, 6.3 mmol). The reaction was stirred at 65° C. for 1 hour. The solvent was then evaporated and the residue was dissolved in ethyl acetate/tetrahydrofuran. The reaction was acidified with 1N hydrochloric acid and the solvents were evaporated. The crude residue was then diluted in methanol (10 mL) and treated with sodium hydroxide (5N, 4.5 mL, 22.7 mmol) at 23° C. and the reaction was stirred overnight. The reaction was then acidified with 1N hydrochloric acid and the solvent was evaporated. The residue was dissolved in N,N-dimethylformamide (8 mL) and precipitated by addition of water. This was allowed to stand at 0° C. The solid was then filtered and dried under high vacuum to give the title material (0.411 g, 50%) as a solid. LC/MS (M+H)+: 361. HPLC ret. time (Condition B): 1.067 min.
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