Methanesulfonyl chloride → 8-[4-((Methylsulfonyl)amino)phenyl]imidazo[1,2-a]pyridine
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[N:10]([CH:14]=[CH:15][N:16]=3)[CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>C(Cl)Cl>[CH3:17][S:18]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]3[N:10]([CH:14]=[CH:15][N:16]=3)[CH:11]=[CH:12][CH:13]=2)=[CH:6][CH:7]=1)(=[O:20])=[O:19]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
Dissolve 4 g (19.1 mmol) of the product from Example 20, in 100 ml of methylene chloride and cool to 0° C. Add 1.6 ml of methanesulfonyl chloride slowly, maintaining the temperature at 5° C. Stir at r.t. for 12 hr. Extract the reaction mixture with 100 ml of 10% sodium hydroxide. Wash with 100 ml of methylene chloride and with 100 ml of ether. Treat with charcoal and neutralize with ammonium chloride. The resulting precipitate is filtered and washed with water to provide the title compound.