2-bromoethylsulfonylbenzene

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

Procedure: 4-Amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamide dihydrochloride (7 g) and 2-(phenylsulfonyl)ethyl bromide (5.6 g) were reacted and treated in the same manner as in Example 199 to give 2.74 g of 4-amino-5-chloro-2-methoxy-N-((1-(2-(phenylsulfonyl)ethyl)-piperidin-4-yl)methyl)benzamide hydrochloride. treated in the same manner as in Example 199

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

Procedure: A mixture of (2-bromo-ethylsulfanyl)-benzene (273 mg, 1.26 mmol) and 3-chlorobenzenecarboperoxoic acid (650 mg, 3.77 mmol) in methylene chloride (5 mL) were stirred at room temperature for 16 h. A saturated sodium sulfite solution was added and the mixture was extracted with methylene chloride. The organic layers were washed by saturated sodium bicarbonate solution, dried over sodium sulfate, and concentrated in vacuo to provide (2-bromo-ethanesulfonyl)-benzene (0.24 g, 76%). the mixture was extracted with methylene chloride The organic layers were washed by saturated sodium bicarbonate solution dried over sodium sulfate concentrated in vacuo

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

Procedure: 4-Amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamide dihydrochloride (7 g) and 2-(phenylsulfonyl)ethyl bromide (5.6 g) were reacted and treated in the same manner as in Example 199 to give 2.74 g of 4-amino-5-chloro-2-methoxy-N-((1-(2-(phenylsulfonyl)ethyl)-piperidin-4-yl)methyl)benzamide hydrochloride. treated in the same manner as in Example 199

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

Procedure: 4-Amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamide dihydrochloride (7 g) and 2-(phenylsulfonyl)ethyl bromide (5.6 g) were reacted and treated in the same manner as in Example 199 to give 2.74 g of 4-amino-5-chloro-2-methoxy-N-((1-(2-(phenylsulfonyl)ethyl)-piperidin-4-yl)methyl)benzamide hydrochloride. treated in the same manner as in Example 199

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

Procedure: A mixture of 3.7 parts of [(2-bromoethyl)sulfonyl]benzene, 4.34 parts of 3-(2-ethoxyethyl)-N-(4-piperidinyl)-3H-imidazo[4,5-b]pyridin-2-amine, 2.5 parts of sodium hydrogen carbonate and 120 parts of ethanol was stirred for 2 hours at reflux temperature. The reaction mixture was filtered over diatomaceous earth and the filtrate was evaporated. The residue was taken up in water and the product was extracted with 4-methyl-2-pentanone. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (97:3 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from a mixture of tetrahydrofuran and 2,2'-oxybispropane. The product was filtered off and dried, yielding 2.6 parts (37.1%) of 3-(2-ethoxyethyl)-N-[1-[2-(phenylsulfonyl)ethyl]-4-piperidinyl]-3H-imidazo-[4,5-b]pyridin-2-amine hemihydrate; mp. 101.9° C. (compound 99). at reflux temperature The reaction mixture was filtered over diatomaceous earth the filtrate was evaporated the product was extracted with 4-methyl-2-pentanone The extract was dried filtered evaporated The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (97:3 by volume) as eluent The pure fractions were collected the eluent was evaporated The residue was crystallized from a mixture of tetrahydrofuran and 2,2'-oxybispropane The product was filtered off dried

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

Procedure: A mixture of (2-bromo-ethylsulfanyl)-benzene (273 mg, 1.26 mmol) and 3-chlorobenzenecarboperoxoic acid (650 mg, 3.77 .mmol) in methylene chloride (5 mL) were stirred at room temperature for 16 h. A saturated sodium sulfite solution was added and the mixture was extracted with methylene chloride. The organic layers were washed by saturated sodium bicarbonate solution, dried over sodium sulfate, and concentrated in vacuo to provide (2-bromo-ethanesulfonyl)-benzene (0.24 g, 76%). the mixture was extracted with methylene chloride The organic layers were washed by saturated sodium bicarbonate solution dried over sodium sulfate concentrated in vacuo

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

Procedure: A mixture of (2-bromo-ethylsulfanyl)-benzene (273 mg, 1.26 mmol) and 3-chlorobenzenecarboperoxoic acid (650 mg, 3.77 mmol) in methylene chloride (5 mL) were stirred at room temperature for 16 h. A saturated sodium sulfite solution was added and the mixture was extracted with methylene chloride. The organic layers were washed by saturated sodium bicarbonate solution, dried over sodium sulfate, and concentrated in vacuo to provide (2-bromo-ethanesulfonyl)-benzene (0.24 g, 76%). the mixture was extracted with methylene chloride The organic layers were washed by saturated sodium bicarbonate solution dried over sodium sulfate concentrated in vacuo

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

Procedure: 4-Amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamide dihydrochloride (7 g) and 2-(phenylsulfonyl)ethyl bromide (5.6 g) were reacted and treated in the same manner as in Example 199 to give 2.74 g of 4-amino-5-chloro-2-methoxy-N-((1-(2-(phenylsulfonyl)ethyl)-piperidin-4-yl)methyl)benzamide hydrochloride. treated in the same manner as in Example 199