33084-49-0|4-Bromo-3-methylisoxazol-5-amine| Ambeed

Structure of 33084-49-0

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Quality Control of [ 33084-49-0 ] Purity: 95% SDS Specification

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Product Details of [ 33084-49-0 ]

CAS No. :	33084-49-0
Formula :	C₄H₅BrN₂O
M.W :	177.00
SMILES Code :	NC1=C(Br)C(C)=NO1
MDL No. :	MFCD09038913

Safety of [ 33084-49-0 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 33084-49-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 33084-49-0 ]

[ 33084-49-0 ] Synthesis Path-Downstream 1~54

1
[ 14678-02-5 ]
[ 33084-49-0 ]

Yield	Reaction Conditions	Operation in experiment
87%	With N-Bromosuccinimide; In chloroform;	(a) 5-Amino-4-bromo-3-methylisoxazole 5-Amino-3-methylisoxazole (0.98 g, 10 mmol) was dissolved in chloroform (15 ml) and cooled to 0 C. N-bromosuccinimide (1.78 g, 10 mmoles) was added in small portions over a period of 10 min. The stirring was continued for another 10 minutes at 0 C. The reaction mixture was diluted with chloroform (50 ml), washed with water (2*50 ml) and the organic layer was dried over magnesium sulfate. Removal of the solvent under reduced pressure gave the crude product which was purified by column chromatography using 9:1, hexanes/ethyl acetate as eluent to give 5-amino-4-bromo-3-methylisoxazole (1.55 g, 87% yield).
87%	With N-Bromosuccinimide; In chloroform;	(a) 5-Amino-4-bromo-3-methylisoxazole 5-Amino-3-methylisoxazole (0.98 g, 10 mmol) was dissolved in chloroform (15 ml) and cooled to 0 C. N-Bromosuccinimide (1.78 g, 10 mmoles) was added in small portions over a period of 10 min. The stirring was continued for another 10 minutes at 0 C. The reaction mixture was diluted with chloroform (50 ml), washed with water (2*50 ml) and the organic layer was dried over magnesium suIfate. Removal of the solvent under reduced pressure gave the crude product which was purified by column chromatography using 9:1, hexanes/ethyl acetate as eluent to give 5-amino-4-bromo-3-methylisoxazole (1.55 g, 87% yield).
87%	With N-Bromosuccinimide; In chloroform;	(a) 5-Amino-4-bromo-3-methylisoxazole 5-Amino-3-methylisoxazole (0.98 g, 10 mmol) was dissolved in chloroform (15 ml) and cooled to 0 C. N-Bromosuccinimide (1.78 g, 10 mmoles) was added in small portions over a period of 10 min. The stirring was continued for another 10 minutes at 0 C. The reaction mixture was diluted with chloroform (50 ml), washed with water (2*50 ml) and the organic layer was dried over magnesium sulfate. Removal of the solvent under reduced pressure gave the crude product, which was purified by column chromatography using 9: 1, hexanes/ethyl acetate as the eluent, to give 5-amino-4-bromo-3-methylisoxazole (1.55 g, 87% yield).

References: [1]Patent: US6342610,2002,B2 .Location in patent: Page column 141.
[2]Patent: US5571821,1996,A .
[3]Patent: US5571821,1996,A .
[4]Patent: US5571821,1996,A .
[5]Bioorganic and medicinal chemistry letters,1996,vol. 6,p. 2393 - 2398.
[6]Journal of Medicinal Chemistry,2009,vol. 52,p. 4370 - 4379.
[7]Journal of Medicinal Chemistry,1997,vol. 40,p. 1682 - 1689.

2
[ 51175-71-4 ]
[ 33084-49-0 ]
N-(4-Bromo-3-methyl-5-isoxazolyl)thiophene-3-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
22%		B. N-(4-Bromo-3-methyl-5-isoxazolyl)thiophene-3-sulfonamide N-(4-Bromo-3-methyl-5-isoxazolyl)thiophene-3-sulfonamide was prepared in the same manner as described in Example 2 from thiophene-3-sulfonyl chloride with <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> in 22% yield. Purification by column chromatography using 10% MeOH/CHCl3 as eluent gave a pale brown oil.

References: [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 2651 - 2656.
[2]Patent: US6342610,2002,B2 .Location in patent: Page column 59.
[3]Patent: US5571821,1996,A .

3
[ 16629-19-9 ]
[ 33084-49-0 ]
N-(4-bromo-3-methyl-5-isoxazolyl)thiophene-2-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34%		EXAMPLE 27 N-(4-Bromo-3-methyl-5-isoxazolyl)-2-thiophenesulfonamide N-(4-Bromo-3-methyl-5-isoxazolyl)-2-thiophenesulfonamide was prepared from <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> and 2-thiophenesulfonyl chloride according to the procedures described in Example 5. The crude product was purified by recrystallization from ethyl acetate/hexanes to give a crystalline solid, m.p. 125-127 C., yield 34%.
34%		EXAMPLE 67 N-(4-Bromo-3-methyl-5-isoxazolyl)-2-thiophenesulfonamide N-(4-Bromo-3-methyl-5-isoxazolyl)-2-thiophenesulfonamide was prepared from <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> and 2-thiophenesulfonyl chloride according to the procedures described in Example 45. The crude product was purified by recrystallization from ethyl acetate/hexanes to give a crystalline solid, m.p. 125-127 C., yield 34%.
	With sodium hydroxide; In tetrahydrofuran; water; mineral oil;	EXAMPLE 9 N-(4-Bromo-3-methyl-5-isoxazolyl)thiophene-2-sulfonamide A solution of <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> (1 77 mg, 1.0 mmol) in dry tetrahydrofuran (THF, 2 ml) was added to a suspension of sodium hydride (60% dispersion in mineral oil, 90 mg, 2.2 mmol) in dry THF (1 ml) at 0-5 C. After stirring at 0-5 C. for 5 min., the reaction was stirred at room temperature for 10 min to complete the reaction. The reaction mixture was re-cooled to 0 C. and thiophene-2-sulfonyl chloride (200 mg, 1.1 mmol) dissolved in dry THF (2 ml) was added dropwise. Stirring was continued for 1 h; during this period the reaction mixture slowly attained ambient temperature. THF was removed under reduced pressure. The residue was dissolved in water (10 ml), the pH was adjusted to 10-11 by adding 5 N sodium hydroxide solution, and was extracted with ethyl acetate (310 ml) to remove the neutral impurities. The aqueous layer was acidified with concentrated HCl (pH 2-3) and extracted with methylene chloride (310 ml). The combined organic layers was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give N-(4-bromo-3-methyl-5-isoxazolyl)thiophene-2-sulfonamide. The pure material was obtained by recrystallization using hexanes/ethyl acetate (110 mg, 34% yield), m.p. 125-127 C.

	With sodium hydroxide; In tetrahydrofuran; water; mineral oil;	EXAMPLE 1 N-(4-Bromo-3-methyl-5-isoxazolyl)thiophene-2-sulfonamide A solution of <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> (177 mg, 1.0 mmol) in dry tetrahydrofuran (THF, 2 ml) was added to a suspension of sodium hydride (60% dispersion in mineral oil, 90 mg, 2.2 mmol) in dry THF (1 ml) at 0-5 C. After stirring at 0-5 C. for 5 min., the reaction was stirred at room temperature for 10 min to complete the reaction. The reaction mixture was re-cooled to 0 C. and thiophene-2-sulfonyl chloride (200 mg, 1.1 mmol) dissolved in dry THF (2 ml) was added dropwise. Stirring was continued for 1 h; during this period the reaction mixture slowly attained ambient temperature. THF was removed under reduced pressure. The residue was dissolved in water (10 ml), the pH was adjusted to 10-11 by adding 5 N sodium hydroxide solution, and was extracted with ethyl acetate (310 ml) to remove the neutral impurities. The aqueous layer was acidified with concentrated HCl (pH 2-3) and extracted with methylene chloride (310 ml). The combined organic layers was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give N-(4-bromo-3-methyl-5-isoxazolyl)thiophene-2-sulfonamide. The pure material was obtained by recrystallization using hexanes/ethyl acetate (110 mg, 34% yield), m.p. 125-127 C.
	With sodium hydroxide; In tetrahydrofuran; water; mineral oil;	EXAMPLE 9 N-(4-Bromo-3-methyl-5-isoxazolyl)thiophene-2-sulfonamide A solution of <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> (177 mg, 1.0 mmol) in dry tetrahydrofuran (THF, 2 ml) was added to a suspension of sodium hydride (60% dispersion in mineral oil, 90 mg, 2.2 mmol) in dry THF (1 ml) at 0-5 C. After stirring at 0-5 C. for 5 min., the reaction was stirred at room temperature for 10 min to complete the reaction. The reaction mixture was re-cooled to 0 C. and thiophene-2-sulfonyl chloride (200 mg, 1.1 mmol) dissolved in dry THF (2 ml) was added dropwise. Stirring was continued for 1 h; during this period the reaction mixture slowly attained ambient temperature. THF was removed under reduced pressure. The residue was dissolved in water (10 ml), the pH was adjusted to 10-11 by adding 5 N sodium hydroxide solution, and was extracted with ethyl acetate (310 ml) to remove the neutral impurities. The aqueous layer was acidified with concentrated HCl (pH 2-3) and extracted with methylene chloride (310 ml). The combined organic layers was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give N-(4-bromo-3-methyl-5-isoxazolyl)thiophene-2-sulfonamide. The pure material was obtained by recrystallization using hexanes/ethyl acetate (110 mg, 34% yield), m.p. 125-127 C.
	With sodium hydroxide; In tetrahydrofuran; water; mineral oil;	EXAMPLE 1 N-(4-Bromo-3-methyl-5-isoxazolyl)thiophene-2-sulfonamide A solution of <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> (177 mg, 1.0 mmol) in dry tetrahydrofuran (THF, 2 ml) was added to a suspension of sodium hydride (60% dispersion in mineral oil, 90 mg, 2.2 mmol) in dry THF (1 ml) at 0-5 C. After stirring at 0-5 C. for 5 min., the reaction was stirred at room temperature for 10 min to complete the reaction. The reaction mixture was re-cooled to 0 C. and thiophene-2-sulfonyl chloride (200 mg, 1.1 mmol) dissolved in dry THF (2 ml) was added dropwise. Stirring was continued for 1 h; during this period the reaction mixture slowly attained ambient temperature. THF was removed under reduced pressure. The residue was dissolved in water (10 ml), the pH was adjusted to 10-11 by adding 5 N sodium hydroxide solution, and was extracted with ethyl acetate (310 ml) to remove the neutral impurities. The aqueous layer was acidified with concentrated HCl (pH 2-3) and extracted with methylene chloride (310 ml). The combined organic layers was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give N-(4-bromo-3-methyl-5-isoxazolyl)thiophene-2-sulfonamide. The pure material was obtained by recrystallization using hexanes/ethyl acetate (110 mg, 34 % yield), m.p. 125-127 C.
	With sodium hydroxide; In tetrahydrofuran; water; mineral oil;	EXAMPLE 1 N-(4-Bromo-3-methyl-5-isoxazolyl)thiophene-2-sulf onamide A solution of <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> (177 mg, 1.0 mmol) in dry tetrahydrofuran (THF, 2 ml) was added to a suspension of sodium hydride (60% dispersion in mineral oil, 90 mg, 2.2 mmol) in dry THF (1 ml) at 0-5 C. After stirring at 0-5 C. for 5 min., the reaction was stirred at room temperature for 10 min to complete the reaction. The reaction mixture was re-cooled to 0 C. and thiophene-2-sulfonyl chloride (200 mg, 1.1 mmol) dissolved in dry THF (2 ml) was added dropwise. Stirring was continued for 1 h; during this period the reaction mixture was slowly attained the ambient temperature. THF was removed under reduced pressure. The residue was dissolved in water (10 ml), the pH was adjusted to 10-11 by adding 5N sodium hydroxide solution, and was extracted with ethyl acetate (310 ml) to remove the neutral impurities. The aqueous layer was acidified with concentrated HCl (pH 2-3) and extracted with methylene chloride (310 ml). The combined organic layers was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give N-(4-bromo-3-methyl-5-isoxazolyl)thiophene-2-sulfonamide. The pure material was obtained by recrystallization using hexanes/ethyl acetate (110 mg, 34 % yield), m.p. 125-127 C.
	With sodium hydroxide; In tetrahydrofuran; water; mineral oil;	EXAMPLE 1 N-(4-Bromo-3-methyl-5-isoxazolyl)thiophene-2-sulfonamide A solution of <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> (177 mg, 1.0 mmol) in dry tetrahydrofuran (THF, 2 ml) was added to a suspension of sodium hydride (60% dispersion in mineral oil, 90 mg, 2.2 mmol) in dry THF (1 ml) at 0-5 C. After stirring at 0-5 C. for 5 min., the reaction was stirred at room temperature for 10 min to complete the reaction. The reaction mixture was re-cooled to 0 C. and thiophene-2-sulfonyl chloride (200 mg, 1.1 mmol) dissolved in dry THF (2 ml) was added dropwise. Stirring was continued for 1 h; during this period the reaction mixture slowly attained ambient temperature. THF was removed under reduced pressure. The residue was dissolved in water (10 ml), the pH was adjusted to 10-11 by adding 5 N sodium hydroxide solution, and was extracted with ethyl acetate (310 ml) to remove the neutral impurities. The aqueous layer was acidified with concentrated HCl (pH 2-3) and extracted with methylene chloride (310 ml). The combined organic layers was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give N-(4-bromo-3-methyl-5-isoxazolyl)thiophene-2-sulfonamide. The pure material was obtained by recrystallization using hexanes/ethyl acetate (110 mg, 34 % yield), m.p. 125-127 C.
	With sodium hydroxide; In tetrahydrofuran; water; mineral oil;	EXAMPLE 9 N-(4-Bromo-3-methyl-5-isoxazolyl)thiophene-2-sulfonamide A solution of <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> (177 mg, 1.0 mmol) in dry tetrahydrofuran (THF, 2 mL) was added to a suspension of sodium hydride (60% dispersion in mineral oil, 90 mg, 2.2 mmol) in dry THF (1 mL) at 0-5 C. After stirring at 0-5 C. for 5 min., the reaction was stirred at room temperature for 10 min to complete the reaction. The reaction mixture was re-cooled to 0 C. and thiophene-2-sulfonyl chloride (200 mg, 1.1 mmol) dissolved in dry THF (2 mL) was added dropwise. Stirring was continued for 1 h; during this period the reaction mixture slowly attained ambient temperature. THF was removed under reduced pressure. The residue was dissolved in water (10 mL), the pH was adjusted to 10-11 by adding 5N sodium hydroxide solution, and was extracted with ethyl acetate (310 mL) to remove the neutral impurities. The aqueous layer was acidified with concentrated HCI (pH 2-3) and extracted with methylene chloride (310 mL). The combined organic layers was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give N-(4-bromo-3-methyl-5-isoxazolyl)thiophene-2-sulfonamide. The pure material was obtained by recrystallization using hexanes/ethyl acetate (110 mg, 34% yield), m.p. 125-127 C.
	With sodium hydroxide; In tetrahydrofuran; water; mineral oil;	EXAMPLE 1 N-(4-Bromo-3-methyl-5-isoxazolyl)thiophene-2-sulfonamide A solution of <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> (177 mg, 1.0 mmol) in dry tetrahydrofuran (THF, 2 ml) was added to a suspension of sodium hydride (60% dispersion in mineral oil, 90 mg, 2.2 mmol) in dry THF (1 ml) at 0-5 C. After stirring at 0-5 C. for 5 min., the reaction was stirred at room temperature for 10 min to complete the reaction. The reaction mixture was re-cooled to 0 C. and thiophene-2-sulfonyl chloride (200 mg, 1.1 mmol) dissolved in dry THF (2 ml) was added dropwise. Stirring was continued for 1 h; during this period the reaction mixture was slowly attained the ambient temperature. THF was removed under reduced pressure. The residue was dissolved in water (10 ml), the pH was adjusted to 10-11 by adding 5N sodium hydroxide solution, and was extracted with ethyl acetate (310 ml) to remove the neutral impurities. The aqueous layer was acidified with concentrated HCl(pH 2-3) and extracted with methylene chloride (310 ml). The combined organic layers was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give N-(4-bromo-3-methyl-5-isoxazolyl)thiophene-2-sulfonamide. The pure material was obtained by recrystallization using hexanes/ethyl acetate (110 mg, 34 % yield), m.p. 125-127 C.

References: [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 2651 - 2656.
[2]Patent: US5514691,1996,A .
[3]Patent: US6342610,2002,B2 .Location in patent: Page column 50.
[4]Patent: US5571821,1996,A .
[5]Patent: US2002/91270,2002,A1 .
[6]Patent: US2002/95041,2002,A1 .
[7]Patent: US6432994,2002,B1 .
[8]Patent: US5962490,1999,A .
[9]Patent: US5591761,1997,A .
[10]Patent: US5594021,1997,A .
[11]Patent: US6248767,2001,B1 .
[12]Patent: US5571821,1996,A .

4
[ 98-60-2 ]
[ 33084-49-0 ]
4-chloro-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%		EXAMPLE 15 4-Chloro-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide 4-Chloro-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide was prepared from <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> and 4-chloro-benzenesulfonyl chloride according to the procedures described in Example 1b. The crude product was purified by recrystallization from ethyl acetate/hexanes to give a yellow powder, m.p. 145-150 C., yield 93%.
93%		EXAMPLE 55 4-Chloro-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide 4-Chloro-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide was prepared from <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> and 4-chlorobenzenesulfonyl chloride according to the procedures described in Example 40b. The crude product was purified by recrystallization from ethyl acetate/hexanes to give a yellow powder, m.p. 145-150 C., yield 93%.

References: [1]Patent: US5514691,1996,A .
[2]Patent: US5571821,1996,A .
[3]Bioorganic and medicinal chemistry letters,1996,vol. 6,p. 2393 - 2398.

5
[ 98-59-9 ]
[ 33084-49-0 ]
N-(4-bromo-3-methyl-5-isoxazolyl)-4-toluenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%		EXAMPLE 17 N-(4-Bromo-3-methyl-5-isoxazolyl)-4-toluenesulfonamide N-(4-Bromo-3-methyl-5-isoxazolyl)-4-toluenesulfonamide was prepared from <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> and 4-toluenesulfonyl chloride according to the procedures described in Example 1b. The crude product was purified by recrystallization from ethyl acetate/hexanes to give off-white crystals, m.p. 169-172 C., yield 69%.
69%		EXAMPLE 57 N-(4-Bromo-3-methyl-5-isoxazolyl)-4-toluenesulfonamide N-(4-Bromo-3-methyl-5-isoxazolyl)-4-toluenesulfonamide was prepared from <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> and 4-toluenesulfonyl chloride according to the procedures described in Example 40b. The crude product was purified by recrystallization from ethyl acetate/hexanes to give off-white crystals, m.p. 169-172 C., yield 69%.

References: [1]Patent: US5514691,1996,A .
[2]Patent: US5571821,1996,A .
[3]Bioorganic and medicinal chemistry letters,1996,vol. 6,p. 2393 - 2398.

6
[ 773-64-8 ]
[ 33084-49-0 ]
2,4,6-trimethyl-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%		EXAMPLE 29 2,4,6-Trimethyl-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide 2,4,6-Trimethyl-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide was prepared from <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> and 2,4,6-trimethylbenzenesulfonyl chloride according to the procedures described in Example 1 b. The crude product was purified by recrystallization from ethyl acetate/hexanes to give a pink solid, m.p. 92-95 C., yield 64%.
64%		EXAMPLE 69 2,4,6-Trimethyl-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide 2,4,6-Trimethyl-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide was prepared from <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> and 2,4,6-trimethylbenzenesulfonyl chloride according to the procedures described in Example 40b. The crude product was purified by recrystallization from ethyl acetate/hexanes to give a pink solid, m.p. 92-95 C., yield 64%.

References: [1]Patent: US5514691,1996,A .
[2]Patent: US5571821,1996,A .
[3]Bioorganic and medicinal chemistry letters,1996,vol. 6,p. 2393 - 2398.

7
[ 98-31-7 ]
[ 33084-49-0 ]
3,4-dichloro-N-(4-bromo-3-methyl-5-isoxazolyl)-benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%		EXAMPLE 40 3,4-Dichloro-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide 3,4-Dichloro-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide was prepared from <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> and 3,4dichlorobenzenesulfonyl chloride according to the procedures described in Example 5. The crude product was purified by recrystallization from ethyl acetate/hexanes to give a crystalline solid, m.p. 144-146 C., yield 60%.
60%		EXAMPLE 80 3,4-Dichloro-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide 3,4-Dichloro-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide was prepared from <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> and 3,4-dichlorobenzenesulfonyl chloride according to the procedures described in Example 45. The crude product was purified by recrystallization from ethyl acetate/hexanes to give a crystalline solid, m.p. 144-146 C., yield 60%.

References: [1]Patent: US5514691,1996,A .
[2]Patent: US5571821,1996,A .
[3]Bioorganic and medicinal chemistry letters,1996,vol. 6,p. 2393 - 2398.

8
[ 1899-93-0 ]
[ 33084-49-0 ]
N-(4-bromo-3-methyl-5-isoxazolyl)-3-toluenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%		EXAMPLE 30 N-(4-bromo-3-methyl-5-isoxazolyl)-3-toluenesulfonamide N-(4-bromo-3-methyl-5-isoxazolyl)-3-toluenesulfonamide was prepared from <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> and 3-toluenesulfonyl chloride according to the procedures described in Example 5. The crude product was purified by recrystallization from ethyl acetate/hexanes to give a crystalline solid, m.p. 138-140 C., yield 63%.
63%		EXAMPLE 70 N-(4-bromo-3-methyl-5-isoxazolyl)-3-toluenesulfonamide N-(4-bromo-3-methyl.5-isoxazolyl)-3-toluenesulfonamide was prepared from <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> and 3-toluenesulfonyl chloride according to the procedures described in Example 45. The crude product was purified by recrystallization from ethyl acetate/hexanes to give a crystalline solid, m.p. 138-140 C., yield 63%.

References: [1]Patent: US5514691,1996,A .
[2]Patent: US5571821,1996,A .
[3]Bioorganic and medicinal chemistry letters,1996,vol. 6,p. 2393 - 2398.

9
[ 2905-21-7 ]
[ 33084-49-0 ]
2-fluoro-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%		EXAMPLE 20 2-Fluoro-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide 2-Fluoro-N-(4-bromo- 3-methyl- 5-isoxazolyl)benzenesulfonamide was prepared from <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> and 2-fluorobenzenesulfonyl chloride according to the procedures described in Example 1b. The crude product was purified by recrystallization from ethyl acetate/hexanes to give a white solid, m.p. 87-89 C., yield 44%.
44%		EXAMPLE 60 2-Fluoro-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide 2-Fluoro-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide was prepared from <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> and 2-fluorobenzenesulfonyl chloride according to the procedures described in Example 40b. The crude product was purified by recrystallization from ethyl acetate/hexanes to give a white solid, m.p. 87-89 C., yield 44%.

References: [1]Patent: US5514691,1996,A .
[2]Patent: US5571821,1996,A .
[3]Bioorganic and medicinal chemistry letters,1996,vol. 6,p. 2393 - 2398.

10
[ 2688-90-6 ]
[ 33084-49-0 ]
N-(4-bromo-3-methyl-5-isoxazolyl)-2-biphenylsulfonamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,1998,vol. 6,p. 2301 - 2316.
[2]Patent: US6342610,2002,B2 .Location in patent: Page column 143.
[3]Bioorganic and medicinal chemistry letters,1996,vol. 6,p. 2393 - 2398.

11
[ 605-65-2 ]
[ 33084-49-0 ]
5-Dimethylamino-N-(4-bromo-3-methyl-5-isoxazolyl)-1-naphthalenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%		EXAMPLE 51 5-Dimethylamino-N-(4-bromo-3-methyl-5-isoxazolyl)-1 -naphthalenesulfonamide 5-Dimethylamino-N-(4-bromo-3-methyl-5-isoxazolyl)-1-naphthalenesulfonamide was prepared from <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> and 5-dimethylaminonaphthalenesulfonyl chloride according to the procedures described in Example 5. The crude product was purified by recrystallization from ethyl acetate/hexanes to give a crystalline solid, m.p. 87-89 C., yield 68%.

References: [1]Patent: US5514691,1996,A .
[2]Bioorganic and medicinal chemistry letters,1996,vol. 6,p. 2393 - 2398.

12
[ 5402-73-3 ]
[ 33084-49-0 ]
2,5-dichloro-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%		EXAMPLE 35 2,5-Dichloro-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide 2,5-Dichloro-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide was prepared from <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> and 2,5-dichlorobenzenesulfonyl chloride according to the procedures described in Example 1 b. The crude product was purified by recrystallization from ethyl acetate/hexanes to give a yellow powder, m.p. 148-150 C., yield 53%.
53%		EXAMPLE 75 2,5-Dichloro-N -(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide 2,5-Dichloro-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide was prepared from <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> and 2,5-dichlorobenzenesulfonyl chloride according to the procedures described in Example 40b. The crude product was purified by recrystallization from ethyl acetate/hexanes to give a yellow powder, m.p. 148-150 C., yield 53%.

References: [1]Patent: US5514691,1996,A .
[2]Patent: US5571821,1996,A .
[3]Bioorganic and medicinal chemistry letters,1996,vol. 6,p. 2393 - 2398.

13
[ 65685-01-0 ]
[ 33084-49-0 ]
N-(4-bromo-3-methyl-5-isoxazolyl)-3-biphenylsulfonamide [ No CAS ]

References: [1]Patent: US6342610,2002,B2 .Location in patent: Page column 144.
[2]Bioorganic and medicinal chemistry letters,1996,vol. 6,p. 2393 - 2398.
[3]Bioorganic and Medicinal Chemistry,1998,vol. 6,p. 2301 - 2316.

14
[ 19040-62-1 ]
[ 33084-49-0 ]
2,5-dimethyl-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%		EXAMPLE 58 2,5-Dimethyl-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide 2,5-Dimethyl-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide was prepared from <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> and 2,5dimethylbenzenesulfonyl chloride according to the procedures described in Example 40b. The crude product was purified by recrystallization from ethyl acetate/hexanes to give off-white crystals, m.p. 102-104 C., yield 81%.

References: [1]Patent: US5571821,1996,A .
[2]Bioorganic and medicinal chemistry letters,1996,vol. 6,p. 2393 - 2398.

15
[ 2905-25-1 ]
[ 33084-49-0 ]
2-bromo-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31%		EXAMPLE 37 2-Bromo-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide 2-Bromo-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide was prepared from <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> and 2-bromobenzenesulfonyl chloride according to the procedures described in Example 5. The crude product was purified by recrystallization from ethyl acetate/hexanes to give a crystalline solid, m.p. 84-86 C., yield 31%.
31%		EXAMPLE 77 2-Bromo-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide 2-Bromo-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide was prepared from <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> and 2-bromobenzenesulfonyl chloride according to the procedures described in Example 45. The crude product was purified by recrystallization from ethyl acetate/hexanes to give a crystalline solid, m.p. 84-86 C., yield 31%.

References: [1]Patent: US5514691,1996,A .
[2]Patent: US5571821,1996,A .
[3]Bioorganic and medicinal chemistry letters,1996,vol. 6,p. 2393 - 2398.

16
[ 16271-33-3 ]
[ 33084-49-0 ]
2,4-dichloro-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%		EXAMPLE 42 2,4-Dichloro-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide 2,4-Dichloro-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide was prepared from <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> and 2,4-dichlorobenzenesulfonyl chloride according to the procedures described in Example 5. The crude product was purified by recrystallization from ethyl acetate/hexanes to give a crystalline solid, m.p. 138-141 C., yield 46%.
46%		EXAMPLE 82 2,4-Dichloro-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide 2,4-Dichloro-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide was prepared from <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> and 2,4-dichlorobenzenesulfonyl chloride according to the procedures described in Example 45. The crude product was purified by recrystallization from ethyl acetate/hexanes to give a crystalline solid, m.p. 138-141 C., yield 46%.

References: [1]Patent: US5514691,1996,A .
[2]Patent: US5571821,1996,A .
[3]Bioorganic and medicinal chemistry letters,1996,vol. 6,p. 2393 - 2398.

17
[ 23095-31-0 ]
[ 33084-49-0 ]
3,4-dimethoxy-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%		EXAMPLE 41 3,4-Dimethoxy-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide 3,4-Dimethoxy-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide was prepared from <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> and 3,4-dimethoxybenzenesulfonyl chloride according to the procedures described in Example 5. The crude product was purified by recrystallization from ethyl acetate/hexanes to give a crystalline solid, m.p. 136-138 C., yield 64 %.
64%		EXAMPLE 81 3,4-Dimethoxy-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide 3,4-Dimethoxy-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide was prepared from <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> and 3,4-dimethoxybenzenesulfonyl chloride according to the procedures described in Example 45. The crude product was purified by recrystallization from ethyl acetate/hexanes to give a crystalline solid, m.p. 136-138 C., yield 64%.

References: [1]Patent: US5514691,1996,A .
[2]Patent: US5571821,1996,A .
[3]Bioorganic and medicinal chemistry letters,1996,vol. 6,p. 2393 - 2398.

18
[ 23095-05-8 ]
[ 33084-49-0 ]
5-bromo-2-methoxy-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%		EXAMPLE 36 5-Bromo-2-methoxy-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide 5-Bromo-2-methoxy-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide was prepared from <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> and 5-bromo-2-methoxybenzenesulfonyl chloride according to the procedures described in Example 5. The crude product was purified by recrystallization from ethyl acetate/hexanes to give a crystalline solid, m.p. 92-195 C., yield 61%.
61%		EXAMPLE 76 5-Bromo-2-methoxy-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide 5-Bromo-2-methoxy-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide was prepared from <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> and 5-bromo-2-methoxybenzenesulfonyl chloride according to the procedures described in Example 45. The crude product was purified by recrystallization from ethyl acetate/hexanes to give a crystalline solid, m.p. 192-195 C., yield 61%.

References: [1]Patent: US5514691,1996,A .
[2]Patent: US5571821,1996,A .
[3]Bioorganic and medicinal chemistry letters,1996,vol. 6,p. 2393 - 2398.

19
[ 80563-86-6 ]
[ 33084-49-0 ]
3-chloro-2-methyl-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34%		EXAMPLE 28 3-Chloro-2-methyl-N-(4-Bromo-3-methyl-5-isoxazolyl)benzenesulfonamide 3-Chloro-2-methyl-N-(4-Bromo-3-methyl-5-isoxazolyl)benzenesulfonamide was prepared from <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> and 3-chloro-2-methylbenzenesulfonyl chloride according to the procedures described in Example 5. The crude product was purified by recrystallization from ethyl acetate/hexanes to give a crystalline solid, m.p. 185-187 C., yield 34 %.
34%		EXAMPLE 68 3-Chloro-2-methyl-N-(4-Bromo-3-methyl-5-isoxazolyl)benzenesulfonamide 3-Chloro-2-methyl-N-(4-Bromo-3-methyl-5-isoxazolyl)benzenesulfonamide was prepared from <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> and 3-chloro-2-methylbenzenesulfonyl chloride according to the procedures described in Example 45. The crude product was purified by recrystallization from ethyl acetate/hexanes to give a crystalline solid, m.p. 185-187 C., yield 34%.

References: [1]Patent: US5514691,1996,A .
[2]Patent: US5571821,1996,A .
[3]Bioorganic and medicinal chemistry letters,1996,vol. 6,p. 2393 - 2398.

20
[ 97272-02-1 ]
[ 33084-49-0 ]
N-(4-bromo-3-methyl-5-isoxazolyl)-5-(phenyl)thiophene-2-sulfonamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 2651 - 2656.
[2]Bioorganic and Medicinal Chemistry,1998,vol. 6,p. 2301 - 2316.

21
[ 185329-81-1 ]
[ 33084-49-0 ]
N-(4-bromo-3-methyl-5-isoxazolyl)-3-(3-tolyl)thiophene-2-sulfonamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 2651 - 2656.
[2]Patent: US6342610,2002,B2 .Location in patent: Page column 132.

22
[ 185329-82-2 ]
[ 33084-49-0 ]
3-p-Tolyl-thiophene-2-sulfonic acid (4-bromo-3-methyl-isoxazol-5-yl)-amide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 2651 - 2656.

23
[ 185329-79-7 ]
[ 33084-49-0 ]
N-(4-bromo-3-methyl-5-isoxazolyl)-3-(2-tolyl)thiophene-2-sulfonamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 2651 - 2656.
[2]Patent: US6342610,2002,B2 .Location in patent: Page column 132.

24
[ 166964-13-2 ]
[ 33084-49-0 ]
N-(4-bromo-3-methyl-5-isoxazolyl)-3-phenoxythiophene-2-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%		C. N-(4-bromo-3-methyl-5-isoxazolyl)-3-phenoxythiophene-2-sulfonamide N-(4-bromo-3-methyl-5-isoxazolyl)-3-phenoxythiophene-2-sulfonamide was prepared from 3-phenoxythiophene-2-sulfonyl chloride and <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> using the method described in Example 1. The product was recrystallized from acetonitrile/H2O to give a solid m.p. 121-123 C., 61% yield.
61%		C. N-(4-bromo-3-methyl-5-isoxazolyl)-3-phenoxythiophene-2-sulfonamide N-(4-bromo-3-methyl-5-isoxazolyl)-3-phenoxythiophene-2-sulfonamide was prepared from 3-phenoxythiophene-2-sulfonyl chloride and <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> using the method described in Example 1. The product was recrystallized from acetonitrile/H2 O to give a solid m.p. 121-123 C., 61% yield.
61%		C. N-(4-bromo-3-methyl-5-isoxazolyl)-3-phenoxythiophene-2-sulfonamide N-(4-bromo-3-methyl-5-isoxazolyl)-3-phenoxythiophene-2-sulfonamide was prepared from 3-phenoxythiophene-2-sulfonyl chloride and <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> using the method described in Example 1. The product was recrystallized from acetonitrile/H2 O to give a solid m.p. 121-123 C., 61% yield.

References: [1]Patent: US2002/95041,2002,A1 .
[2]Patent: US5962490,1999,A .
[3]Patent: US5594021,1997,A .
[4]Patent: US6342610,2002,B2 .Location in patent: Page column 71.
[5]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 2651 - 2656.

25
[ 185329-86-6 ]
[ 33084-49-0 ]
N-(4-bromo-3-methyl-5-isoxazolyl)-3-(4-ethylphenyl)thiophene-2-sulfonamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 2651 - 2656.
[2]Patent: US6342610,2002,B2 .Location in patent: Page column 132.

26
[ 185329-88-8 ]
[ 33084-49-0 ]
N-(4-bromo-3-methyl-5-isoxazolyl)-3-(4-iso-propylphenyl)thiophene-2-sulfonamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 2651 - 2656.
[2]Patent: US6342610,2002,B2 .Location in patent: Page column 132.

27
[ 185329-87-7 ]
[ 33084-49-0 ]
N-(4-bromo-3-methyl-5-isoxazolyl)-3-(4-propylphenyl)thiophene-2-sulfonamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 2651 - 2656.
[2]Patent: US6342610,2002,B2 .Location in patent: Page column 132.

28
[ 185329-84-4 ]
[ 33084-49-0 ]
N-(4-bromo-3-methyl-5-isoxazolyl)-3-(3-methoxyphenyl)thiophene-2-sulfonamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 2651 - 2656.
[2]Patent: US6342610,2002,B2 .Location in patent: Page column 132.

29
[ 185329-85-5 ]
[ 33084-49-0 ]
3-(4-Methoxy-phenyl)-thiophene-2-sulfonic acid (4-bromo-3-methyl-isoxazol-5-yl)-amide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 2651 - 2656.

30
[ 185329-92-4 ]
[ 33084-49-0 ]
N-(4-bromo-3-methyl-5-isoxazolyl)-3-(2,4-dimethylphenyl)thiophene-2-sulfonamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 2651 - 2656.
[2]Patent: US6342610,2002,B2 .Location in patent: Page column 132.

31
[ 185329-89-9 ]
[ 33084-49-0 ]
N-(4-bromo-3-methyl-5-isoxazolyl)-3-(4-butylphenyl)-thiophene-2-sulfonamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 2651 - 2656.
[2]Patent: US6342610,2002,B2 .Location in patent: Page column 132.

32
[ 185329-83-3 ]
[ 33084-49-0 ]
N-(4-bromo-3-methyl-5-isoxazolyl)-3-(2-methoxyphenyl)thiophene-2-sulfonamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 2651 - 2656.
[2]Patent: US6342610,2002,B2 .Location in patent: Page column 132.

33
[ 185329-93-5 ]
[ 33084-49-0 ]
N-(4-bromo-3-methyl-5-isoxazolyl)-3-(2-methyl-4-propylphenyl)thiophene-2-sulfonamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 2651 - 2656.
[2]Patent: US6342610,2002,B2 .Location in patent: Page column 132.

34
[ 185329-94-6 ]
[ 33084-49-0 ]
N-(4-bromo-3-methyl-5-isoxazolyl)-3-[4-iso-butyl-2-(methylphenyl)thiophene]-2-sulfonamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 2651 - 2656.
[2]Patent: US6342610,2002,B2 .Location in patent: Page column 132.

35
[ 33084-49-0 ]
[ 133-59-5 ]
N-(4-bromo-3-methyl-5-isoxazolyl)-2-toluenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%		EXAMPLE 19 N-(4-Bromo-3-methyl-5-isoxazolyl)-2-toluenesulfonamide N-(4-Bromo-3-methyl-5-isoxazolyl)-2-toluenesulfonamide was prepared from <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> and 2-toluenesulfonyl chloride according to the procedures described in Example 1b. The crude product was purified by recrystallization from ethyl acetate/hexanes to give white crystalline solid, m.p. 93-96 C., yield 88%.
88%		EXAMPLE 59 N-(4-Bromo-3-methyl-5-isoxazolyl)-2-toluenesulfonamide N-(4-Bromo-3-methyl-5-isoxazolyl)-2-toluenesulfonamide was prepared from <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> and 2-toluenesulfonyl chloride according to the procedures described in Example 40b. The crude product was purified by recrystallization from ethyl acetate/hexanes to give white crystalline solid, m.p. 93-96 C., yield 88%.

References: [1]Patent: US5514691,1996,A .
[2]Patent: US5571821,1996,A .
[3]Bioorganic and medicinal chemistry letters,1996,vol. 6,p. 2393 - 2398.

36
[ 59337-92-7 ]
[ 33084-49-0 ]
[ 184035-14-1 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 933 - 938.
[2]Patent: US6342610,2002,B2 .Location in patent: Page column 54.
[3]Journal of Medicinal Chemistry,1997,vol. 40,p. 1682 - 1689.
[4]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 2093 - 2098.

37
[ 184041-68-7 ]
[ 33084-49-0 ]
N-(4-bromo-3-methyl-5-isoxazolyl)-2-[(4-methyl)phenethyl]thiophene-3-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%		C. N-(4-bromo-3-methyl-5-isoxazolyl)-2-[(4-methyl)phenethyl]thiophene-3-sulfonamide N-(4-bromo-3-methyl-5-isoxazolyl)-2-[(4-methyl)phenethyl]thiophene-3-sulfonamide was prepared, as described in Example 10, using 2-[(4-methyl)-phenethyl]thiophene-3-sulfonylchloride and <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> in 52% yield.
52%		C. N-(4-bromo-3-methyl-5-isoxazolyl)-2-[(4-methyl)phenethyl]thiophene-3-sulfonamide N-(4-bromo-3-methyl-5-isoxazolyl)-2-[(4-methyl)phenethyl]thiophene-3-sulfonamide was prepared, as described in Example 10, using 2-[(4-methyl)-phenethyl]thiophene-3-sulfonylchloride and <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> in 52% yield.
52%		C. N-(4-bromo-3-methyl-5-isoxazolyl)-2-[(4-methyl)phenethyl]thiophene-3-sulfonamide N-(4-bromo-3-methyl-5-isoxazolyl)-2-[(4-methyl)phenethyl]thiophene-3-sulfonamide was prepared, as described in Example 2, using 2-[(4-methyl)phenethyl]thiophene-3-sulfonylchloride and <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> in 52% yield.

52%

C. N-(4-Bromo-3-methyl-5-isoxazolyl)-2-[(4-methyl)phenethyl]thiophene-3-sulfonamide N-(4-Bromo-3-methyl-5-isoxazolyl)-2-[(4-methyl)phenethyl]thiophene-3-sulfonamide was prepared, as described in Example 10, using 2-[(4-methyl)phenethyl]thiophene-3-sulfonyl chloride and <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> in 52% yield.

References: [1]Patent: US2002/91270,2002,A1 .
[2]Patent: US6432994,2002,B1 .
[3]Patent: US5962490,1999,A .
[4]Patent: US6248767,2001,B1 .
[5]Patent: US6342610,2002,B2 .Location in patent: Page column 118.
[6]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 939 - 944.

38
[ 184041-74-5 ]
[ 33084-49-0 ]
N-(4-Bromo-3-methyl-5-isoxazolyl)-2-[(4-methylphenoxy)methyl]-thiophene-3-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%		C. N-(4-bromo-3-methyl-5-isoxazolyl)-2-[(4-methylphenoxy)methyl]thiophene-3-sulfonamide N-(4-bromo-3-methyl-5-isoxazolyl)-2-[(4-methylphenoxy)methyl]thiophene-3-sulfonamide was prepared, as described in Example 2, by reacting 3-chlorosulfonyl-2-[(4-methylphenoxy)methyl]thiophene with <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong>, resulting in a 64% yield, m.p. 128-130 C.
64%		C. N-(4-bromo-3-methyl-5-isoxazolyl)-2-[(4-methylphenoxy)methyl]thiophene-3-sulfonamide N-(4-bromo-3-methyl-5-isoxazolyl)-2-[(4-methylphenoxy)methyl]thiophene-3-sulfonamide was prepared, as described in Example 2, by reacting 3-chlorosulfonyl-2-[(4-methylphenoxy)methyl]thiophene with <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong>, resulting in a 64% yield, m.p. 128-130 C.
64%		C. N-(4-Bromo-3-methyl-5-isoxazolyl)-2-[(4-methylphenoxy)methyl]-thiophene-3-sulfonamide N-(4-Bromo-3-methyl-5-isoxazolyl)-2-[(4-methylphenoxy)methyl]-thiophene-3-sulfonamide was prepared, as described in Example 10, by reacting 3-chlorosulfonyl-2-[(4-methylphenoxy)methyl]thiophene with <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong>, resulting in a 64% yield, m.p. 128-130 C.

References: [1]Patent: US5962490,1999,A .
[2]Patent: US5594021,1997,A .
[3]Patent: US6248767,2001,B1 .
[4]Patent: US6342610,2002,B2 .Location in patent: Page column 119.
[5]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 933 - 938.

39
[ 190521-60-9 ]
[ 33084-49-0 ]
N-(4-bromo-3-methyl-5-isoxazolyl)-3-[(2,4-dimethylphenoxy)methyl]thiophene-2-sulfonamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 933 - 938.

40
[ 190521-62-1 ]
[ 33084-49-0 ]
N-(4-bromo-3-methyl-5-isoxazolyl)-3-[(2,4,6-trimethylphenoxy)methyl]thiophene-2-sulfonamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 933 - 938.

41
3-(Benzo[1,3]dioxol-5-yloxymethyl)-thiophene-2-sulfonyl chloride [ No CAS ]
[ 33084-49-0 ]
N-(4-bromo-3-methyl-5-isoxazolyl)-3-[3,4-(methylenedioxy)phenoxy]methyl}-thiophene-2-sulfonamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 933 - 938.

42
5-Dimethylamino-2-methyl-benzenesulfonyl chloride [ No CAS ]
[ 33084-49-0 ]
N-(4-Bromo-3-methyl-isoxazol-5-yl)-5-dimethylamino-2-methyl-benzenesulfonamide [ No CAS ]

References: [1]Journal of Organic Chemistry,1998,vol. 63,p. 2348 - 2350.

43
[ 1623-93-4 ]
[ 33084-49-0 ]
[ 166964-10-9 ]

References: [1]Bioorganic and Medicinal Chemistry,1998,vol. 6,p. 2301 - 2316.
[2]Patent: US6342610,2002,B2 .Location in patent: Page column 141.

44
[ 97272-01-0 ]
[ 33084-49-0 ]
N-(4-bromo-3-methyl-5-isoxazolyl)-5-benzylthiophene-2-sulfonamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,1998,vol. 6,p. 2301 - 2316.
[2]Patent: US6342610,2002,B2 .Location in patent: Page column 73.

45
5-Chlorosulphonyl-2,2'-bithiophene [ No CAS ]
[ 33084-49-0 ]
N-(4-bromo-3-methyl-5-isoxazolyl)-5-(thien-2-yl)thiophene-2-sulfonamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,1998,vol. 6,p. 2301 - 2316.
[2]Patent: US6342610,2002,B2 .Location in patent: Page column 58.

46
2-(2-methyl-5-furyl)thiophene-5-sulfonyl chloride [ No CAS ]
[ 33084-49-0 ]
N-(4-bromo-3-methyl-5-isoxazolyl)-5-(2-methyl-5-furyl)thiophene-2-sulfonamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,1998,vol. 6,p. 2301 - 2316.
[2]Patent: US6342610,2002,B2 .Location in patent: Page column 99.

47
[ 166964-03-0 ]
[ 33084-49-0 ]
N-(4-Bromo-3-methyl-5-isoxazolyl)-5-(4-ethylphenyl)thiophene-2-sulfonamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,1998,vol. 6,p. 2301 - 2316.
[2]Patent: US6342610,2002,B2 .Location in patent: Page column 61.

48
[ 814-49-3 ]
[ 33084-49-0 ]
N-(4-bromo-3-methyl-5-isoxazolyl)diethylphosphoramidate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%		N-(4-bromo-3-methyl-5-isoxazolyl)diethyl phosphoramidate was prepared by the method of Example 3 with 4-bromo-3-methyl-5-amino isoxazole (0.27 g, 1.5 mmol), THF (8 ml), NaH (60% oil dispersion, 0.15 g, 3.8 mmol) and diethyl chlorophosphate (0.25 ml, 1.7 mmol). Recrystallization two times from chloroform and hexanes provided 0.24 g (51%) of light yellow crystals, m.p. 78-80 C.
	With NaH; In tetrahydrofuran;	EXAMPLE 5 N-(4-bromo-3-methyl-5-isoxazolyl)diethylphosphoramidate N-(4-bromo-3-methyl-5-isoxazolyl)diethyl phosphoramidate was prepared by the method of Example 3 with 4-bromo-3-methyl-5-amino isoxazole (0.27 g, 1.5 mmol), THF (8 ml), NaH (60% oil dispersion, 0.15 g, 3.8 mmol) and diethyl chlorophosphate (0.25 ml, 1.7 mmol). Recrystallization two times from chloroform and hexanes provided 0.24 g (51%) of light yellow crystals, m.p. 78-80 C.

References: [1]Patent: US6384261,2002,B1 .Location in patent: Page column 28.
[2]Patent: US5958905,1999,A .

49
2-(3-phenylsulfonyl)thiophene sulfonyl chloride [ No CAS ]
[ 33084-49-0 ]
N-(4-bromo-3-methyl-5-isoxazolyl)-5-(benzenesulfonyl)thiophene-2-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%		EXAMPLE 15 N-(4-Bromo-3-methyl-5-isoxazolyl)-5-(benzenesulfonyl)thiophene-2-sulfonamide N-(4-Bromo-3-methyl-5-isoxazolyl)-5-(benzenesulfonyl)thiophene-2-sulfonamide was prepared: in the same manner as described in Example 2 from <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> and 5-benzenesulfonylthiophene-2-sulphonyl chloride in 59% yield. Purification was achieved by recrystallization from ethyl acetate/hexanes to give a crystalline solid, m.p. 139-142 C.

References: [1]Patent: US6342610,2002,B2 .Location in patent: Page column 53.
[2]Patent: US5571821,1996,A .

50
[ 15084-51-2 ]
[ 33084-49-0 ]
4-tert-butyl-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
21%	In tetrahydrofuran; methanol; water; mineral oil;	EXAMPLE 39 4-tert-Butyl-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide A solution of <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> (354 mg, 2.0 mmol) in dry THF (1 ml) was added to a suspension of sodium hydride (60% dispersion in mineral oil, 188 mg, 4.4 mmol) in dry THF (1 ml) at 0-5 C. After stirring at 0-5 C. for 10 min., the reaction was warmed to room temperature for 10 min. to complete the reaction. The reaction mixture was re-cooled to 0 C. and 4-tert-butylbenzenesulfonyl chloride (512 mg, 2.2 mmol) was added slowly. Stirring was continued for 20 min. at 0-5 C. Excess sodium hydride was decomposed by addition of methanol (0.4 ml) followed by water (0.5 ml). The mixture was acidified with hydrochloric acid and extracted with dichloromethane. The extract was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure to give a crude product, which was purified by recrystallization from ethyl acetate/hexanes to give a white solid in 21% yield, m.p. 170 C. (dec.).
21%	In tetrahydrofuran; methanol; water; mineral oil;	EXAMPLE 5 4-tert-Butyl-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide A solution of <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> (354 mg, 2.0 mmol) in dry THF (1 ml) was added to a suspension of sodium hydride (60% dispersion in mineral oil, 188 mg, 4.4 mmol)in dry THF (1 ml) at 0-5 C. After stirring at 0-5 C. for 10 min., the reaction was warmed to room temperature for 10 min. to complete the reaction. The reaction mixture was re-cooled to 0 C. and 4-tert-butylbenzenesulfonyl chloride (512 mg, 2.2 mmol) was added slowly. Stirring was continued for 20 min. at 0-5 C. Excess sodium hydride was decomposed by addition of methanol (0.4 ml) followed by water (0.5 ml). The mixture was acidified with hydrochloric acid and extracted with dichloromethane. The extract was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure to give a crude product, which was purified by recrystallization from ethyl acetate/hexanes to give a white solid in 21% yield, m.p. 170 C. (dec.).
21%	In tetrahydrofuran; methanol; water; mineral oil;	EXAMPLE 39 4-tert-Butyl-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide A solution of <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> (354 mg, 2.0 mmol) in dry THF (1 ml) was added to a suspension of sodium hydride (60% dispersion in mineral oil, 188 mg, 4.4 mmol) in dry THF (1 ml) at 0-5 C. After stirring at 0-5 C. for 10 min., the reaction was warmed to room temperature for 10 min. to complete the reaction. The reaction mixture was re-cooled to 0 C. and 4-tert-butylbenzenesulfonyl chloride (512 mg, 2.2 mmol) was added slowly. Stirring was continued for 20 min. at 0-5 C. Excess sodium hydride was decomposed by addition of methanol (0.4 ml) followed by water (0.5 ml). The mixture was acidified with hydrochloric acid and extracted with dichloromethane. The extract was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure to give a crude product, which was purified by recrystallization from ethyl acetate/hexanes to give a white solid in 21% yield, m.p. 170 C. (dec.).

21%

In tetrahydrofuran; methanol; water; mineral oil;

EXAMPLE 45 4-tert-Butyl-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide A solution of <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> (354 mg, 2.0 mmol) in dry THF (1 ml) was added to a suspension of sodium hydride (60% dispersion in mineral oil, 188 mg, 4.4 mmol) in dry THF (1 ml) at 0-5 C. After stirring at 0-5 C. for 10 min., the reaction was warmed to room temperature for 10 min. to complete the reaction. The reaction mixture was re-cooled to 0 C. and 4-tert-butylbenzenesulfonyl chloride (512 mg, 2.2 mmol) was added slowly. Stirring was continued for 20 min. at 0-5 C. Excess sodium hydride was decomposed by addition of methanol (0.4 ml) followed by water (0.5 ml). The mixture was acidified with hydrochloric acid and extracted with dichloromethane. The extract was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure to give a crude product, which was purified by recrystallization from ethyl acetate/hexanes to give a white solid in 21% yield, m.p. 170 C. (dec.).

References: [1]Patent: US5962490,1999,A .
[2]Patent: US5514691,1996,A .
[3]Patent: US5594021,1997,A .
[4]Patent: US6342610,2002,B2 .Location in patent: Page column 64.
[5]Patent: US5571821,1996,A .

51
[ 52665-48-2 ]
[ 33084-49-0 ]
N-(4-bromo-3-methyl-5-isoxazolyl)furan-2-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20%	With NaH;	EXAMPLE 69 N-(4-Bromo-3-methyl-5-isoxazolyl)furan-2-sulfonamide N-(4-bromo-3-methyl-5-isoxazolyl)furan-2-sulfonamide was prepared by the method of Example 1 with 5-amino-4-bromo-3-methyl-isoxazole (0.266 g, 1.5 mmol), NaH (60% oil dispersion) (0.15 g, 3.8 mmol) and furan-2-sulfonyl chloride (Example 36A) (0.30 mg, 1.8 mmol). Flash chromatography (50% EtOAc/hexane) and recrystallization from CHCl3 and hexane provided 90 mg (20% yield) of light yellow crystals (m.p. 117-119 C.).
20%	With NaH;	EXAMPLE 69 N-(4-Bromo-3-methyl-5-isoxazolyl)furan-2-sulfonamide N-(4-bromo-3-methyl-5-isoxazolyl)furan-2-sulfonamide was prepared by the method of Example 1 with <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> (0.266 g, 1.5 mmol), NaH (60% oil dispersion) (0.15 g, 3.8 mmol) and furan-2-sulfonyl chloride (Example 36A) (0.30 mg, 1.8 mmol). Flash chromatography (50% EtOAc/hexane) and recrystallization from CHCl3 and hexane provided 90 mg (20% yield) of light yellow crystals (m.p. 117-119 C.).
20%	With NaH;	EXAMPLE 69 N-(4-Bromo-3-methyl-5-isoxazolyl)furan-2-sulfonamide N-(4-bromo-3-methyl-5-isoxazolyl)furan-2-sulfonamide was prepared by the method of Example 1 with <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> (0.266 g, 1.5 mmol), NaH (60% oil dispersion) (0.15 g, 3.8 mmol) and furan-2-sulfonyl chloride (Example 36A) (0.30 mg, 1.8 mmol). Flash chromatography (50% EtOAc/hexane) and recrystallization from CHCl3 and hexane provided 90 mg (20% yield) of light yellow crystals (m.p. 117-119 C.).

References: [1]Patent: US2002/95041,2002,A1 .
[2]Patent: US5962490,1999,A .
[3]Patent: US5594021,1997,A .
[4]Patent: US6342610,2002,B2 .Location in patent: Page column 78.

52
[ 90273-31-7 ]
[ 33084-49-0 ]
N-(4-bromo-3-methyl-5-isoxazolyl)-2-methylbenzo[b]thiophene-3-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With NaH; In tetrahydrofuran; water;	EXAMPLE 41 N-(4-Bromo-3-methyl-5-isoxazolyl)-2-methylbenzo[b]thiophene-3-sulfonamide NaH (60% oil dispersion, 2.5 mmoles, 100 mg) was added to a solution of <strong>[33084-49-0]4-bromo-3-methyl-5-aminoisoxazole</strong> (1.0 mmoles, 0.177 g). THF (5 ml) at 0 C. was added, and the resulting reaction mixture was stirred 10 min at 0 C. 2-Methylbenzo[b]thiophene-3-sulfonyl chloride (1.2 mmoles, 0.28 g) was added, and the reaction mixture was stirred for 20 min at 0 C., then warmed to ambient temperature for 1 hr followed by addition of 2 ml of water. The mixture was diluted with ethyl acetate (100 ml) and washed with 2% HCl (2*50 ml), then brine (50 ml). The organic phase was dried (MgSO4), filtered and concentrated. Recrystallization of the crude reaction mixture resulted in 0.24 g (63%) of N-(4-bromo-3-methyl-5-isoxazolyl)-2-methylbenzo[b]thiophene-3-sulfonamide as an off-white solid, m.p. 131-133 C.
	With NaH; In tetrahydrofuran; water;	EXAMPLE 41 N-(4-Bromo-3-methyl-5-isoxazolyl)-2-methylbenzo[b]thiophene-3-sulfonamide NaH (60% oil dispersion, 2.5 mmoles, 100 mg) was added to a solution of <strong>[33084-49-0]4-bromo-3-methyl-5-aminoisoxazole</strong> (1.0 mmoles, 0.177 g). THF (5 ml) at 0 C. was added, and the resulting reaction mixture was stirred 10 min at 0 C. 2-Methylbenzo[b]thiophene-3-sulfonyl chloride (1.2 mmoles, 0.28 g) was added, and the reaction mixture was stirred for 20 min at 0 C., then warmed to ambient temperature for 1 hr followed by addition of 2 ml of water. The mixture was diluted with ethyl acetate (100 ml) and washed with 2% HCl (2*50 ml), then brine (50 ml). The organic phase was dried (MgSO4), filtered and concentrated. Recrystallization of the crude reaction mixture resulted in 0.24 g (63%) of N-(4-bromo-3-methyl-5-isoxazolyl)-2-methylbenzo[b]thiophene-3-sulfonamide as an off-white solid, m.p. 131-133 C.

References: [1]Patent: US6342610,2002,B2 .Location in patent: Page column 65.
[2]Patent: US5962490,1999,A .
[3]Patent: US5594021,1997,A .

53
[ 184039-66-5 ]
[ 33084-49-0 ]
N-(4-bromo-3-methyl-5-isoxazolyl)-2-benzylbenzo[b]thiophene-3-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With NaH; In tetrahydrofuran;	C. N-(4-bromo-3-methyl-5-isoxazolyl)-2-benzylbenzo[b]thiophene-3-sulfonamide N-(4-bromo-3-methyl-5-isoxazolyl)-2-benzylbenzo[b]thiophene-3-sulfonamide was prepared by the method of Example 41 with <strong>[33084-49-0]4-bromo-3-methyl-5-aminoisoxazole</strong> (1.0 mmoles, 0.177 g), NaH (2.5 mmoles, 100 mg), 2-benzylbenzo[b]thiophene-3-sulfonyl chloride (1.2 mmoles, 0.39 g) and THF (7 ml). Flash chromatography (5% methanol/chloroform) followed by recrystallization from chloroform and hexanes provided 0.11 g (24%) of a tan crystalline solid, m.p. 120-123 C.
	With NaH; In tetrahydrofuran;	C. N-(4-bromo-3-methyl-5-isoxazolyl)-2-benzylbenzo[b]thiophene-3-sulfonamide N-(4-bromo-3-methyl-5-isoxazolyl)-2-benzylbenzo[b]thiophene-3-sulfonamide was prepared by the method of Example 41 with <strong>[33084-49-0]4-bromo-3-methyl-5-aminoisoxazole</strong> (1.0 mmoles, 0.177 g), NaH (2.5 mmoles, 100 mg), 2-benzylbenzo[b]thiophene-3-sulfonyl chloride (1.2 mmoles, 0.39 g) and THF (7 ml). Flash chromatography (5% methanol/chloroform) followed by recrystallization from chloroform and hexanes provided 0.11 g (24%) of a tan crystalline solid, m.p. 120-123 C.

References: [1]Patent: US6342610,2002,B2 .Location in patent: Page column 66.
[2]Patent: US5962490,1999,A .
[3]Patent: US5594021,1997,A .

54
2-n-butylbenzo[b]thiophene-3-sulfonyl chloride [ No CAS ]
[ 33084-49-0 ]
N-(4-bromo-3-methyl-5-isoxazolyl)-2-n-butylbenzo[b]thiophene-3-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With NaH; In tetrahydrofuran;	C. N-(4-bromo-3-methyl-5-isoxazolyl)-2-n-butylbenzo[b]thiophene-3-sulfonamide N-(4-bromo-3-methyl-5-isoxazolyl)-2-n-butylbenzo[b]thiophene-3-sulfonamide was prepared by the method of Example 41 with <strong>[33084-49-0]4-bromo-3-methyl-5-aminoisoxazole</strong> (1.0 mmoles, 0.177 g), NaH (2.5 mmoles, 100 mg), 2-n-butylbenzo[b]thiophene-3-sulfonyl chloride (1.2 mmoles, 0.35 g) and THF (6 ml). Recrystallization from ethyl acetate and hexanes provided 0.24 g (56%) of a yellow solid, m.p. 124.5-126 C.
	With NaH; In tetrahydrofuran;	C. N-(4-bromo-3-methyl-5-isoxazolyl)-2-n-butylbenzo[b]thiophene-3-sulfonamide N-(4-bromo-3-methyl-5-isoxazolyl)-2-n-butylbenzo[b]thiophene-3-sulfonamide was prepared by the method of Example 41 with <strong>[33084-49-0]4-bromo-3-methyl-5-aminoisoxazole</strong> (1.0 mmoles, 0.177 g), NaH (2.5 mmoles, 100 mg), 2-n-butylbenzo[b]thiophene-3-sulfonyl chloride (1.2 mmoles, 0.35 g) and THF (6 ml). Recrystallization from ethyl acetate and hexanes provided 0.24 g (56%) of a yellow solid, m.p. 124.5-126 C.

References: [1]Patent: US6342610,2002,B2 .Location in patent: Page column 66.
[2]Patent: US5962490,1999,A .
[3]Patent: US5594021,1997,A .

Historical Records

Technical Information

• Alkyl Halide Occurrence • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • General Reactivity • Grignard Reaction • Hiyama Cross-Coupling Reaction • Hydride Reductions • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Leuckart-Wallach Reaction • Mannich Reaction • Petasis Reaction • Preparation of Amines • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Dihalides • Specialized Acylation Reagents-Vilsmeier Reagent • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Ugi Reaction

Related Functional Groups of
[ 33084-49-0 ]

Bromides

A125487 [166964-06-3]

4-Bromo-3-(tert-butyl)isoxazol-5-amine

Similarity: 0.86

A577428 [101084-19-9]

4-Bromo-3-methylisoxazole

Similarity: 0.80

Amines

A125487 [166964-06-3]

4-Bromo-3-(tert-butyl)isoxazol-5-amine

Similarity: 0.86

Related Parent Nucleus of
[ 33084-49-0 ]

Isoxazoles

A125487 [166964-06-3]

4-Bromo-3-(tert-butyl)isoxazol-5-amine

Similarity: 0.86

A577428 [101084-19-9]

4-Bromo-3-methylisoxazole

Similarity: 0.80

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
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P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
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P270	Do not eat, drink or smoke when using this product.
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P281	Use personal protective equipment as required.
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Code	Phrase
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P320
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P321
P322
P330	Rinse mouth.
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P342	If experiencing respiratory symptoms:
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P363	Wash contaminated clothing before reuse.
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P373	DO NOT fight fire when fire reaches explosives.
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P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
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P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
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P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
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P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
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P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 33084-49-0

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CAS No.: 33084-49-0

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[ 33084-49-0 ] Synthesis Path-Downstream 1~54

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[ 33084-49-0 ]

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[ 33084-49-0 ]

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{[proInfo.proName]}

CAS No.: 33084-49-0

{[proInfo.proName]}

CAS No.: 33084-49-0

Alternative Products

Product Details of [ 33084-49-0 ]

Safety of [ 33084-49-0 ]

Application In Synthesis of [ 33084-49-0 ]

[ 33084-49-0 ] Synthesis Path-Downstream 1~54

Related Products

Historical Records

Technical Information

Categories

Related Functional Groups of [ 33084-49-0 ]

Bromides

Amines

Related Parent Nucleus of [ 33084-49-0 ]

Isoxazoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Molarity Calculator

Total Compounds Calculator

Dissolution Calculator

Related Functional Groups of
[ 33084-49-0 ]

Related Parent Nucleus of
[ 33084-49-0 ]