(2,3-dichlorophenyl)methanesulfonyl chloride

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: By using 5-(4-aminophenyl)-1,5,8,9,10,11-hexahydronaphtho[1,2-b][1,4]diazepine-2,4-dione (32 mg, 0.100 mmol) obtained in Example 55, and (2,3-dichlorophenyl)methanesulfonyl chloride (31 mg, 0.119 mmol), the title compound (50 mg, yield 92%) was obtained in the same manner as that of Example 145.

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: (2,3-dichlorophenyl)-methanesulfonic acid (260 mg, 1.0 mmole) was dissolved in 5 mL dry THF and cooled to 0° C. A catalytic drop of DMF was added followed by oxalyl chloride (0.44 mL, 5.0 mmole). The reaction mixture was allowed to warm to room temperature over 90 minutes and then filtered through Celite®, rinsing the Celite® with an additional 15 mL dry THF. The filtrate was evaporated to a volume of ca. 5 mL and then 5 mL water was added in small portions, cooling the vessel in a water bath. The mixture was extracted with 2×25 mL EtOAc and the combined organics were washed with saturated sodium bicarbonate, brine, and dried (MgSO4). Filtration and evaporation gives the crude product as a yellow oil. Chromatography on silica gel using a gradient of 5% EtOAc/Hexane to 30% EtOAc/Hexane gives 142 mg (2,3-dichlorophenyl)-methanesulfonyl chloride as a white solid.1H NMR (400 MHz, CHLOROFORM-D) δ ppm 5.09 (s, 2 H) 7.25 (t, J=7.96 Hz, 1 H) 7.45 (m, 1 H) 7.53 (dd, J=8.08, 1.52 Hz, 1 H) to warm to room temperature over 90 minutes filtered through Celite® rinsing the Celite® with an additional 15 mL dry THF The filtrate was evaporated to a volume of ca. 5 mL 5 mL water was added in small portions cooling the vessel in a water bath The mixture was extracted with 2×25 mL EtOAc the combined organics were washed with saturated sodium bicarbonate, brine dried (MgSO4) Filtration and evaporation gives the crude product as a yellow oil

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: (2,3-dichlorophenyl)-methanesulfonic acid (260 mg, 1.0 mmole) was dissolved in 5 mL dry THF and cooled to 0° C. A catalytic drop of DMF was added followed by oxalyl chloride (0.44 mL, 5.0 mmole). The reaction mixture was allowed to warm to room temperature over 90 minutes and then filtered through Celite®, rinsing the Celite® with an additional 15 mL dry THF. The filtrate was evaporated to a volume of ca. 5 mL and then 5 mL water was added in small portions, cooling the vessel in a water bath. The mixture was extracted with 2×25 mL EtOAc and the combined organics were washed with saturated sodium bicarbonate, brine, and dried (MgSO4). Filtration and evaporation gives the crude product as a yellow oil. Chromatography on silica gel using a gradient of 5% EtOAc/Hexane to 30% EtOAc/Hexane gives 142 mg (2,3-dichlorophenyl)-methanesulfonyl chloride as a white solid.1H NMR (400 MHz, CHLOROFORM-D) δ ppm 5.09 (s, 2 H) 7.25 (t, J=7.96 Hz, 1 H) 7.45 (m, 1 H) 7.53 (dd, J=8.08, 1.52 Hz, 1 H) to warm to room temperature over 90 minutes filtered through Celite® rinsing the Celite® with an additional 15 mL dry THF The filtrate was evaporated to a volume of ca. 5 mL 5 mL water was added in small portions cooling the vessel in a water bath The mixture was extracted with 2×25 mL EtOAc the combined organics were washed with saturated sodium bicarbonate, brine dried (MgSO4) Filtration and evaporation gives the crude product as a yellow oil

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: By using 5-(4-aminophenyl)-1,5,8,9,10,11-hexahydronaphtho[1,2-b][1,4]diazepine-2,4-dione (32 mg, 0.100 mmol) obtained in Example 55, and (2,3-dichlorophenyl)methanesulfonyl chloride (31 mg, 0.119 mmol), the title compound (50 mg, yield 92%) was obtained in the same manner as that of Example 145.