Water → HCID 23654206, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(5,6-dihydroxy-benzoimidazol-1-yl)-4-phenyl-thiazole-5-carboxylic acid ethyl ester (118.8 mg, 0.31 mmol, intermediate for Example 39), bromoethyl methyl ether (0.1 ml) and potassium carbonate (200 mg) in N-methylpyrrolidone (2 ml) was stirred at RT overnight and 80° C. for 4 hr. Water was added, and the mixture was extracted with ethyl acetate. After removal of solvent, the residue was diluted with methanol (3 ml) and sodium hydroxide solution (1N, 1.5 ml) was added. The mixture was stirred at RT for 105 min. Methanol was removed, the aqueous was neutralized to pH 3. The precipitate was collected and purified by preparative HPLC to give the desired product (24.6 mg, yield 17%). 1H-NMR (DMSO-D6) 8.71 (s, 1H); 8.20-8.27 (m, 2H); 7.83 (s, 1H); 7.24-7.41 (m, 3H); 4.17-4.22 (m, 4H); 3.66-3.75 (m, 4H); 3.33 (s, 6H). MS M/z 470 (M+1).

Provenance & Evidence