N-butylbenzenesulfonamide

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium hydride (0.029 g, 0.0012 mol, 1.1 equiv) was suspended in DMF (5 mL). N-Butyl-benzenesulfonamide (0.256 g, 0.222 mL, 0.0012 mol. 1.2 equiv) was then added and stirred at room temperature for 10 minutes. To the resulting mixture was then added the 2-chloro-N-methyl benzimidazole, (0.166 g, 0.001 mol). The resulting mixture was heated to 50° C. and stirred overnight (16 hours). The resulting mixture was then poured into water (15 mL) and stirred for 1 hour. The resulting solution was extracted with DCM (20 mL) and the organic layer was separated. The organic layer was washed with 1N NaOH (20 mL), and brine (20 mL), then dried over Na2SO4 and evaporated under reduced pressure. The resulting residue was purified by reverse phase HPLC (eluent 60-80% acetonitrile) to yield the title compound as a yellowish solid. MS 343.4 The resulting mixture was heated to 50° C. stirred overnight (16 hours) stirred for 1 hour The resulting solution was extracted with DCM (20 mL) the organic layer was separated The organic layer was washed with 1N NaOH (20 mL), and brine (20 mL) dried over Na2SO4 evaporated under reduced pressure The resulting residue was purified by reverse phase HPLC (eluent 60-80% acetonitrile)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium hydride (0.029 g, 0.0012 mol, 1.1 equiv) was suspended in DMF (5 mL). N-Butyl-benzenesulfonamide (0.256 g, 0.222 mL, 0.0012 mol. 1.2 equiv) was then added and stirred at room temperature for 10 minutes. To the resulting mixture was then added the 2-chloro-N-methyl benzimidazole, (0.166 g, 0.001 mol). The resulting mixture was heated to 50° C. and stirred overnight (16 hours). The resulting mixture was then poured into water (15 mL) and stirred for 1 hour. The resulting solution was extracted with DCM (20 mL) and the organic layer was separated. The organic layer was washed with 1N NaOH (20 mL), and brine (20 mL), then dried over Na2SO4 and evaporated under reduced pressure. The resulting residue was purified by reverse phase HPLC (eluent 60-80% acetonitrile) to yield the title compound as a yellowish solid. MS 343.4 The resulting mixture was heated to 50° C. stirred overnight (16 hours) stirred for 1 hour The resulting solution was extracted with DCM (20 mL) the organic layer was separated The organic layer was washed with 1N NaOH (20 mL), and brine (20 mL) dried over Na2SO4 evaporated under reduced pressure The resulting residue was purified by reverse phase HPLC (eluent 60-80% acetonitrile)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium hydride (0.029 g, 0.0012 mol, 1.1 equiv) was suspended in DMF (5 mL). N-Butyl-benzenesulfonamide (0.256 g, 0.222 mL, 0.0012 mol. 1.2 equiv) was then added and stirred at room temperature for 10 minutes. To the resulting mixture was then added the 2-chloro-N-methyl benzimidazole, (0.166 g, 0.001 mol). The resulting mixture was heated to 50° C. and stirred overnight (16 hours). The resulting mixture was then poured into water (15 mL) and stirred for 1 hour. The resulting solution was extracted with DCM (20 mL) and the organic layer was separated. The organic layer was washed with 1N NaOH (20 mL), and brine (20 mL), then dried over Na2SO4 and evaporated under reduced pressure. The resulting residue was purified by reverse phase HPLC (eluent 60-80% acetonitrile) to yield the title compound as a yellowish solid. MS 343.4 The resulting mixture was heated to 50° C. stirred overnight (16 hours) stirred for 1 hour The resulting solution was extracted with DCM (20 mL) the organic layer was separated The organic layer was washed with 1N NaOH (20 mL), and brine (20 mL) dried over Na2SO4 evaporated under reduced pressure The resulting residue was purified by reverse phase HPLC (eluent 60-80% acetonitrile)