2-(4-chlorophenyl)ethanesulfonyl chloride

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: A mixture of (S)-2-methyl-6-nitro-2-(piperazin-1-ylmethyl)-2,3-dihydroimidazo[2,1-b]oxazole dihydrochloride prepared in Example 408 (236 mg, 0.88 mmol) and DMF (3 ml) was added potassium carbonate (500 mg, 3.62 mmol) and 2-(4-chlorophenyl)ethanesulfonyl chloride (240 mg, 1 mmol) in this order followed by stirring at room temperature overnight. To the reaction mixture, water was added, and the solution was extracted with ethyl acetate. The organic phase was washed with water three times and saturated saline solution, dried over sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/methanol=50/1) to afford (S)-2-{4-[2-(4-chlorophenyl)ethanesulfonyl]piperazin-1-ylmethyl}-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole (100 mg, yield 26%) as a white powder. the solution was extracted with ethyl acetate The organic phase was washed with water three times and saturated saline solution dried over sodium sulfate filtered The filtrate was concentrated under reduced pressure The residue was purified by silica gel column chromatography (methylene chloride/methanol=50/1)

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

Procedure: A mixture of (S)-2-methyl-6-nitro-2-(piperazin-1-ylmethyl)-2,3-dihydroimidazo[2,1-b]oxazole dihydrochloride prepared in Example 408 (236 mg, 0.88 mmol) and DMF (3 ml) was added potassium carbonate (500 mg, 3.62 mmol) and 2-(4-chlorophenyl)ethanesulfonyl chloride (240 mg, 1 mmol) in this order followed by stirring at room temperature overnight. To the reaction mixture, water was added, and the solution was extracted with ethyl acetate. The organic phase was washed with water three times and saturated saline solution, dried over sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/methanol=50/1) to afford (S)-2-{4-[2-(4-chlorophenyl)ethanesulfonyl]piperazin-1-ylmethyl}-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole (100 mg, yield 26%) as a white powder. the solution was extracted with ethyl acetate The organic phase was washed with water three times and saturated saline solution dried over sodium sulfate filtered The filtrate was concentrated under reduced pressure The residue was purified by silica gel column chromatography (methylene chloride/methanol=50/1)

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

Procedure: from 2-(4-chlorophenyl)-ethanesulphonyl chloride and ethyl 2-[4-(2-aminoethyl)-phenoxy]-2-methylpropionate; colorless oil; yield 77% of theory, and from this, by hydrolysis: yield 77% of theory, and from this, by hydrolysis

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: from 2-(4-chlorophenyl)-ethanesulphonyl chloride and ethyl 2-[4-(2-aminoethyl)-phenoxy]-2-methylpropionate; colorless oil; yield 77% of theory, and from this, by hydrolysis: yield 77% of theory, and from this, by hydrolysis

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

Procedure: 2-Aminobenzenesulfonamide (0.52 g, 3 mmol) was dissolved in pyridine (20 mL) followed by addition of 2-(4-chlorophenyl)ethanesulfonyl chloride (0.80 g, 3.3 mmol) and the reaction was stirred at RT overnight. The solvent was then removed under reduced pressure and the crude material was purified by preparative HPLC (XTerra MS C8 column, acetonitrile/ammonium acetate buffer) to give the title compound (87 mg, 8%) as a white solid. The solvent was then removed under reduced pressure the crude material was purified by preparative HPLC (XTerra MS C8 column, acetonitrile/ammonium acetate buffer)

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

Procedure: 2-Aminobenzenesulfonamide (0.52 g, 3 mmol) was dissolved in pyridine (20 mL) followed by addition of 2-(4-chlorophenyl)ethanesulfonyl chloride (0.80 g, 3.3 mmol) and the reaction was stirred at RT overnight. The solvent was then removed under reduced pressure and the crude material was purified by preparative HPLC (XTerra MS C8 column, acetonitrile/ammonium acetate buffer) to give the title compound (87 mg, 8%) as a white solid. The solvent was then removed under reduced pressure the crude material was purified by preparative HPLC (XTerra MS C8 column, acetonitrile/ammonium acetate buffer)

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

Procedure: To a solution of 2-amino-5-methoxy-benzenesulfonamide (4.0 g, 19.80 mmol) in pyridine (60 mL), 2-(4-chloro-phenyl)-ethanesulfonyl chloride (4.73 g, 19.79 mmol) was added slowly at 0° C. The reaction mixture was stirred at RT for 16 h and then concentrated under reduced pressure at 35° C. The residue was then partitioned between ethyl acetate and 1N HCl. The organic layer was separated, dried over sodium sulfate and concentrated in vacuo. The crude product was purified by flash column chromatography using ethyl acetate/hexane (1:1) to give the title compound (7.1 g, 88%). concentrated under reduced pressure at 35° C The residue was then partitioned between ethyl acetate and 1N HCl The organic layer was separated dried over sodium sulfate concentrated in vacuo The crude product was purified by flash column chromatography

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

Procedure: A mixture of (S)-2-methyl-6-nitro-2-(piperazin-1-ylmethyl)-2,3-dihydroimidazo[2,1-b]oxazole dihydrochloride prepared in Example 408 (236 mg, 0.88 mmol) and DMF (3 ml) was added potassium carbonate (500 mg, 3.62 mmol) and 2-(4-chlorophenyl)ethanesulfonyl chloride (240 mg, 1 mmol) in this order followed by stirring at room temperature overnight. To the reaction mixture, water was added, and the solution was extracted with ethyl acetate. The organic phase was washed with water three times and saturated saline solution, dried over sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/methanol=50/1) to afford (S)-2-{4-[2-(4-chlorophenyl)ethanesulfonyl]piperazin-1-ylmethyl}-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole (100 mg, yield 26%) as a white powder. the solution was extracted with ethyl acetate The organic phase was washed with water three times and saturated saline solution dried over sodium sulfate filtered The filtrate was concentrated under reduced pressure The residue was purified by silica gel column chromatography (methylene chloride/methanol=50/1)