Imidazole 1-methanesulfonyl

Chlorophenethyl alcohol N-Bromosuccinimide Peracetic acid Potassium carbonate Imidazole Triethylamine Sodium hydroxide Methanesulfonyl chloride... 

S)-l-[2-Hydroxy-4-(4-chlorophenyl)butyl]-lH-imidazole nitrate was prepared as follows. To a solution of (2S)-l-(p-toluenesulphonyloxy)-4-(4-chlorophenyl)butan-2-ol (250 mg, 1 mmol) in THF (5 ml) at 0°C was added triethylamine (0.28 ml, 2.0 mmol), followed by methanesulfonyl chloride (0,15 ml, 2.0 mmol). The reaction mixture was was warmed to room temperature and stirred for 1 h. The mixture was poured into aq. NaHC03, extracted with EtOAC, and the organic phase dried and evaporated to dryness. The resulting mesylate was dissolved in acetone (50 ml), then 2,6-dichlorobenzenethiol... 

Alkylation of (585b) with a phenacyl bromide produced (589), which can be cyclized with hydrazine to (590) (77JHC59). Similar cyclizations have been carried out on a 1-phenacyl-2-brpmoimidazole derivative (74UKZ99), a l-phenacyl-2-methanesulfonyl-imidazole derivative (74CHE1492) and l-(2-chloroethyl)-2-bromo-4,5-diphenylimidazole (75CHE371) to afiford imidazo[2,l-c][l,2,4]triazines. 

Scheme 17 Synthesis of polyamine-imidazole conjugates. Reagents and conditions a aminoalcohol, CFI2CI2, 2h, rt b methanesulfonyl chloride, pyridine, 30 min, rt c 211, DMSO, 32h, 70 °C d 212, DMSO, 5h, 50 °C e 1 1 TFA CH2Cl2, 1 h, rt / NaOH then CH2CI2, chromatography g 20% Pd(OH)2/C, H2, MeOH, 4h ii H2O, HCl/EtOH, 3h, 0 °C then rt [246]...

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