2-phenylbenzenesulfonyl chloride

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: N-(4-Chloro-3-methyl-5-isoxazolyl)-2-biphenylsulfonamide was prepared in the same manner as described in Example 10 from 5-amino-4-chloro-3-methylisoxazole and 2-biphenylsulfonyl chloride in 74% yield. Purification was achieved by recrystallization from ethyl acetate/hexanes to give a crystalline solid, m.p. 132-134° C. Purification was achieved by recrystallization from ethyl acetate/hexanes to give a crystalline solid, m.p. 132-134° C.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: N-(4-bromo-3-methyl-5-isoxazolyl)-2-biphenylsulfonamide was prepared in the same manner as described in Example 8b from 5-amino-4-bromo-3-methylisoxazole and 2-biphenylsulfonyl chloride in 71% yield. Purification was achieved by recrystallization from ethyl acetate/hexanes to give a crystalline solid, m.p. 145-147° C. Purification was achieved by recrystallization from ethyl acetate/hexanes to give a crystalline solid, m.p. 145-147° C.

反応条件: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2-Bromobiphenyl (2.33 g, 10 mmol) was dissolved in ether (10 ml) and cooled to -78° C. n-Butyllithium (2.5 M solution in hexane, 4.8 ml, 12 mmol) was added dropwise under constant stirring and an argon atmosphere. The resultant reaction mixture was stirred at -70° C. to -60° C. for 1 h. The reaction mixture was cooled to -78° C. and sulfuryl chloride (0.88 ml, 11 mmol) was added dropwise. After addition, the reaction mixture was allowed to attain ambient temperature slowly and stirred for 1 h. The reaction mixture was diluted with ethyl acetate (50 ml), washed with water and the organic layer dried over anhydrous MgSO4. Removal of the solvent under reduced pressure gave a crude product, which was purified by column chromatography, using hexane followed by 5% ethyl acetate in hexane as eluent, to give 2-bi-phenylsulfonyl chloride as a solid (1.3 g, 51% yield). was added dropwise The resultant reaction mixture was stirred at -70° C. to -60° C. for 1 h After addition to attain ambient temperature stirred for 1 h washed with water the organic layer dried over anhydrous MgSO4 Removal of the solvent under reduced pressure gave a crude product, which was purified by column chromatography

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Sodium hydride (60% dispersion in oil; 0.198 g) was suspended in dimethoxyethane (5 ml) and 2-amino-5-bromo-3-methoxypyrazine (0.405 g) was added with stirring. After 15 minutes, 2-biphenylsulphonyl chloride (0.5 g) was added and the mixture was stirred for 18 hours. The reaction mixture was poured into water (20 ml) and acidified to pH2 with concentrated hydrochloric acid and extracted with ethyl acetate (3×25 ml). The combined organic extracts were evaporated and the residue was purified by flash chromatography on silica gel (30 g), eluting with hexane/ethyl acetate/glacial acetic acid (160/40/1 v/v), to give N-(5-bromo-3-methoxy-2-pyrazinyl)-2-biphenylsulphonamide (0.46 g); 1H NMR (d6 -DMSO): 3.82(s,3H), 7.2-7.4(m,6H), 7.53-7.7(m,2H), 7.78(s,1H), 8.08(dd,1H), 10.33(br,1H); mass spectrum (+ve FAB, methanol/NBA): 420(M+H)+. the mixture was stirred for 18 hours extracted with ethyl acetate (3×25 ml) The combined organic extracts were evaporated the residue was purified by flash chromatography on silica gel (30 g) eluting with hexane/ethyl acetate/glacial acetic acid (160/40/1 v/v)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 2-biphenylsulphonyl chloride (0.31 g), 3-amino-6-chloropyridazine (0.5 g) in pyridine (5 ml) was stirred for 18 hours. Volatile material was removed by evaporation and 1M sodium hydroxide solution (4 ml) and methanol (10 ml) were added. The reaction mixture was stirred on a steam bath for 20 minutes and, after cooling, volatile material was again removed by evaporation. The residue was dissolved in water (100 ml) and acidified with concentrated hydrochloric acid to pH 1-2 and extracted with ethyl acetate (3×50 ml). The combined extracts were dried (MgSO4) and evaporated to give a solid. The solid was recrystallised twice from isopropanol to give 2-phenyl-N-(6-chloro-3-pyridazinyl)benzenesulphonamide (0.08 g), m.p. 196°-198° C.; mass spectrum (+ve FAB, methanol/dichloromethane/NBA): 346 (M+H)+. Volatile material was removed by evaporation and 1M sodium hydroxide solution (4 ml) and methanol (10 ml) were added after cooling volatile material was again removed by evaporation The residue was dissolved in water (100 ml) extracted with ethyl acetate (3×50 ml) The combined extracts were dried (MgSO4) evaporated to give a solid The solid was recrystallised twice from isopropanol

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The title prophetic compound may be synthesized using biphenylsulfonylchloride and Intermediate 35. MS (ESI) mass calcd. for C26H24N4O2S, 456.16. The title prophetic compound may be synthesized

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The title prophetic compound may be synthesized using biphenylsulfonylchloride and Intermediate 35. MS (ESI) mass calcd. for C26H24N4O2S, 456.16. The title prophetic compound may be synthesized

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: N-(4-Chloro-3-methyl-5-isoxazolyl)-2-biphenylsulfonamide was prepared in the same manner as described in Example 10 from 5-amino-4-chloro-3-methylisoxazole and 2-biphenylsulfonyl chloride in 74% yield. Purification was achieved by recrystallization from ethyl acetate/hexanes give a crystalline solid, m.p. 132-134° C. Purification was achieved by recrystallization from ethyl acetate/hexanes give a crystalline solid, m.p. 132-134° C.