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CAS No. : | 184040-74-2 | MDL No. : | MFCD18642943 |
Formula : | C9H7ClN2O5S2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BFHXYQAPYRDEDW-UHFFFAOYSA-N |
M.W : | 322.75 | Pubchem ID : | 10805820 |
Synonyms : |
|
Num. heavy atoms : | 19 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.11 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 6.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 68.43 |
TPSA : | 146.12 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.0 cm/s |
Log Po/w (iLOGP) : | 1.2 |
Log Po/w (XLOGP3) : | 1.79 |
Log Po/w (WLOGP) : | 3.09 |
Log Po/w (MLOGP) : | 0.5 |
Log Po/w (SILICOS-IT) : | 1.68 |
Consensus Log Po/w : | 1.65 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 1.0 |
Egan : | 1.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -3.09 |
Solubility : | 0.26 mg/ml ; 0.000805 mol/l |
Class : | Soluble |
Log S (Ali) : | -4.48 |
Solubility : | 0.0108 mg/ml ; 0.0000333 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -3.36 |
Solubility : | 0.142 mg/ml ; 0.00044 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 3.25 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
F. N-(4-chloro-3-methyl-5-isoxazolyl)-2-[3,4-(methylenedioxy)-6-(2-acetoxyethoxy)]phenylaminocarbonyl-3-thiophenesulfonamide N-(4-chloro-3-methyl-5-isoxazolyl)-2-[3,4-(methylenedioxy)-6-(2-acetoxyethoxy)]phenylaminocarbonyl-3-thiophenesulfonamide was synthesised in the same manner as Example 87 using 1-acetoxy-2-[3,4-(methylenedioxy)-6-aminophenoxy]ethane and <strong>[184040-74-2]N-(4-chloro-3-methyl-5-isoxazolyl)-2-carboxylthiophene-3-sulfonamide</strong>. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; | Step 1: Preparation of Compound 10 3[(4-chloro-3-methyl-5-isoxazolyl)amino]sulfonyl}-2-thiophenecarboxylic acid To a 500 mL round bottom flask containing 46.5 g of 3-[(4-chloro-3-methyl-5-isoxazolyl)amino]sulfonyl}-2-thiophenecarboxylic acid methyl ester was added 250 mL of 1 N sodium hydroxide. The mixture was stirred until no starting material remained. The reaction solution was acidified with 2 N hydrochloric acid, ethyl acetate extracted (3*100 mL). The combined extracts were dried (MgSO4), filterred and condensed by rotary evaporation to yield 42.5 g of compound 10 as a solid. | |
Step 2 3-(4-Chloro-3-methyl-isoxazol-5-ylsulfamoyl)-thiophene-2-carboxylic acid: At about 0 C., sodium hydride (60% dispersion in mineral oil, 458 mg, 19 mmol) was added to a solution of 5-amino-4-chloro-3-methylisoxazole (1.1 g, 8.3 mmol) in anhydrous tetrahydrofuran (30 mL). The resulting mixture was stirred for about 10 minutes and 2-(methoxycarbonyl)thiophene-3-sulfonyl chloride (1.95 g, 8.11 mmol) was slowly added. Under continuous stirring, the mixture was maintained at ambient temperature for about 4 hours. The mixture was then diluted with hexanes (30 mL) and the resulting precipitate was filtered and washed with hexanes. The precipitate was then dissolved in 1 N sodium hydroxide and stirred at ambient temperature for about 1 hour. After acidifying to pH ~2 with 2 N hydrochloric acid, the resulting precipitate was filtered, washed with water, and dried in vacuo to give the desired product 3-[(4-chloro-3-methyl-5-isoxazolyl)sulfamoyl]-2-thiophenecarboxylic acid (1.2 g, 45%) as a yellow powder. 1H NMR (300 MHz, CD3OD) δ 7.82 (d, J=5.4 Hz, 1H), 7.53 (d, J=5.4 Hz, 1H), 2.24 (s, 3H); LC-MS: m/z=323 (MH)+. | ||
With water; sodium hydroxide; In methanol; at 20℃; for 5h; | To a mixture of sodium hydride (60%, 2.1 g, 52 mmol) and tetrahydrofuran (20 mL) was added a mixture of 4-chloro-3-methyl-1,2-oxazol-5-amine (3.0 g, 23 mmol) and tetrahydrofuran (20 mL) at 0 C., followed by stirring at that temperature for 30 minutes. Methyl 3-(chlorosulfonyl)thiophene-2-carboxylate (5.3 g, 22 mmol) was added at that temperature to the reaction mixture, which was then stirred for 1 hour at 0 C., and then stirred for 4 hours at room temperature. Hexane (100 ml) was added at room temperature to the reaction mixture, and the precipitated solid was collected by filtration. Methanol (20 mL) was added to the solid, followed by a 2N aqueous solution of sodium hydroxide (20 mL), and the reaction mixture was stirred for 5 hours at room temperature. The solvent was distilled away under reduced pressure, and ice water (20 mL) was added to the residue, followed by a 2 N aqueous solution of hydrochloric acid (20 mL). The precipitated solid was collected by filtration to give the title compound (2.5 g, 35% yield). 1H-NMR Spectrum (DMSO-d6) δ (ppm): 2.16 (3H, d, J=1.8 Hz), 7.45 (1H, dd, J=1.3, 5.3 Hz), 7.95 (1H, dd, J=0.9, 5.3 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With n-butyllithium; In tetrahydrofuran; hexane; | A. N-(4-Chloro-3-methyl-5-isoxazolyl)-3-sulfamoyl-5-methyl-2-thiophenecarboxylic acid To a solution of <strong>[184040-74-2]N-(4-chloro-3-methyl-5-isoxazolyl)-3-sulfamoyl-2-thiophenecarboxylic acid</strong> (6 g, 18.60 mmol) in anhydrous tetrahydrofuran (240 mL) at -78 C. and under nitrogen was added nBuLi (2.5 M in hexane, 30 mL, 74.4 mmol). The mixture was stirred at this temperature for 2 h before the addition of iodomethane (6.6 g, 74.4 mmol). The mixture was then poured into crushed ice and then allowed to warm to room temperature. After acidification with concentrated HCl to pH ~1, the mixture was extracted with ethyl acetate (2*200 mL). The organic layers were combined, dried (MgSO4), the solids were filtered and the filtrate was concentrated to give N-(4-chloro-3-methyl-5-isoxazolyl)-3-sulfamoyl-5-methyl-2-thiophenecarboxylic acid and the starting material in about a 2:1 ratio (8.5 g combined weight). | |
With n-butyllithium; In tetrahydrofuran; hexane; | A. N-(4-Chloro-3-methyl-5-isoxazolyl)-3-sulfamoyl-5-methyl-2-thiophenecarboxylic acid To a solution of <strong>[184040-74-2]N-(4-chloro-3-methyl-5-isoxazolyl)-3-sulfamoyl-2-thiophenecarboxylic acid</strong> (6 g, 18.60 mmol) in anhydrous tetrahydrofuran (240 mL) at -78 C. and under nitrogen was added nBuLi (2.5 M in hexane, 30 mL, 74.4 mmol). The mixture was stirred at this temperature for 2 h before the addition of iodomethane (6.6 g, 74.4 mmol). The mixture was then poured into crushed ice and then allowed to warm to room temperature. After acidification with concentrated HCl to pH ~1, the mixture was extracted with ethyl acetate (2*200 mL). The organic layers were combined, dried (MgSO4), the solids were filtered and the filtrate was concentrated to give N-(4-chloro-3-methyl-5-isoxazolyl)-3-sulfamoyl-5-methyl-2-thiophenecarboxylic acid and the starting material in about a 2:1 ratio (8.5 g combined weight). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dicyclohexyl-carbodiimide; In dichloromethane; ethyl acetate; for 16h; | Example 1: Preparation of the Compound of Formula (II).[0045] To a solution of 20.0 g of the compound of Formula (IV) in 200 ml EtOAc and 100 ml DCM was added 13.O g DCC. After stirring for 16 hours the reaction mixture was filtered through a silica gel plug and the silica gel plug was washed with EtOAc, followed by concentration in vacuo. The crude was recrystallized form 400 ml hot EtOAC:Hexanes (1 :1) go give 13.8 g of the title compound has on off white crystalline material. 1H NMR (400 MHz, CDCl3): δ 2.24 (s, 3H), 7.32 (d, J = 5.1 Hz, IH), 7.83 (d, J = 5.1 Hz, IH) ppm. MS (ESI) m/z: 304.96 [MH-H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
15% | With pyridine; 1,1'-carbonyldiimidazole; In N,N-dimethyl-formamide; | EXAMPLE 150 N-(4-chloro-3-methyl-5-isoxazolyl)-2-[(2-methyl-1,3,4-thiadiazol-5-yl)aminocarbonyl]thiophene-3-sulfonamide Carbonyldiimidazole (553 mg, 3.4 lmmol) was added to a solution of N-(4-chloro-3-methyl-5-isoxazolyl)-2-carboxyl-thiophene-3-sulfonamide (10 g, 3.1 mmol) in dry DMF (1.0 ml). The mixture was stirred at room temperature for 15 minutes before the sequential addition of 2-amino-5-methyl-1,3,4-thiadiazole (736 mg, 6.2 mmol) and pyridine (10 ml). The resulting mixture was stirred at room temperature overnight. To work up, the reaction mixture was poured into 1 N HCl (150 ml) and extracted with EtOAc. The organic layer was dried (MgSO4), the solid was filtered and the filtrate was concentrated. The residue was purified via HPLC to give N-(4-chloro-3-methyl-5-isoxazolyl)-2-[(2-methyl-1,3,4-thiadiazol-5-yl)aminocarbonyl]thiophene-3-sulfonamide as a white powder (15% yield, m.p. 192-194 C.). |
15% | With pyridine; 1,1'-carbonyldiimidazole; In N,N-dimethyl-formamide; | EXAMPLE 150 N-(4-chloro-3-methyl-5-isoxazolyl)-2-[(2-methyl-1,3,4-thiadiazol-5-yl)aminocarbonyl]thiophene-3-sulfonamide Carbonyldiimidazole (553 mg, 3.41mmol) was added to a solution of N-(4-chloro-3-methyl-5-isoxazolyl)-2-carboxyl-thiophene-3-sulfonamide (1.0 g, 3.1 mmol) in dry DMF (10 ml). The mixture was stirred at room temperature for 1 5 minutes before the sequential addition of 2-amino-5-methyl-1,3,4-thiadiazole (736 mg, 6.2 mmol) and pyridine (10 ml). The resulting mixture was stirred at room temperature overnight. To work up, the reaction mixture was poured into 1N HCl (150 ml) and extracted with EtOAc. The organic layer was dried (MgSO4), the solid was filtered and the filtrate was concentrated. The residue was purified via HPLC to give N-(4-chloro-3-methyl-5-isoxazolyl)-2-[(2-methyl-1,3,4-thiadiazol-5-yl)aminocarbonyl]thiophene-3-sulfonamide as a white powder (15% yield, m.p. 192-194 C.). |
15% | With pyridine; 1,1'-carbonyldiimidazole; In N,N-dimethyl-formamide; | EXAMPLE 150 N-(4-chloro-3-methyl-5-isoxazolyl)-2-[(2-methyl-1,3,4-thiadiazol-5-yl)aminocarbonyl]thiophene-3-sulfonamide Carbonyldiimidazole (553 mg, 3.41mmol) was added to a solution of N-(4-chloro-3-methyl-5-isoxazolyl)-2-carboxyl-thiophene-3-sulfonamide (10 g, 3.1 mmol) in dry DMF (10 ml). The mixture was stirred at room temperature for 15 minutes before the sequential addition of 2-amino-5-methyl-1,3,4-thiadiazole (736 mg, 6.2 mmol) and pyridine (10 ml). The resulting mixture was stirred at room temperature overnight. To work up, the reaction mixture was poured into 1NHCl (150 ml) and extracted with EtOAc. The organic layer was dried (MgSO4), the solid was filtered and the filtrate was concentrated. The residue was purified via HPLC to give N-(4-chloro-3-methyl-5-isoxazolyl)-2-[(2-methyl-1,3,4-thiadiazol-5-yl)aminocarbonyl]thiophene-3-sulfonamide as a white powder (15% yield, m.p. 192-194 C.). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With NaH; 1,1'-carbonyldiimidazole; In N,N-dimethyl-formamide; mineral oil; | EXAMPLE 148 N-(4-chloro-3-methyl-5-isoxazolyl)2-[2-acetyl-4,5-(methylenedioxy)phenyl]aminocarbonyl}thiophene-3-sulfonamide Carbonyldiimidazole (553 mg, 3.41 mmol) was added to a solution of <strong>[184040-74-2]N-(4-chloro-3-methyl-5-isoxazolyl)-2-carboxylthiophene-3-sulfonamide</strong> (1.0 g, 3.1 mmol) in dry DMF (10 ml). The mixture was stirred at room temperature for 15 minutes to give mixture (I). NaH (60% dispersion in mineral oil, 521 mg, 13.02 mmol) was added to a solution of 2'-amino-4',5'-(methylenedioxy)acetophenone (1.13 g, 6.2 mmol) in dry DMF (10 ml) at 0 C. The mixture was stirred at 0 C. for 15 minutes to give mixture (II). Mixture (I) was slowly cannulated into mixture (II) at 0 C. The resulting mixture was stirred at 0 C. for 4 hours. The reaction mixture was poured into 2 N HCl (aq., 200 ml) and the resulting precipitate was filtered. The solid was washed with water (2*10 ml) and ethyl ether (2*10 ml) to give N-(4-chloro-3-methyl-5-isoxazolyl)2-[2-acetyl-4,5-(methylenedioxy)phenyl]aminocarbonyl}thiophene-3-sulfonamide (730 mg, 49% yield) as a dull yellow powder, m.p. 191-193 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With NaH; In N,N-dimethyl-formamide; mineral oil; | EXAMPLE 148 N-(4-chloro-3-methyl-5-isoxazolyl) 2-{›2-acetyl-4,[5-(methylenedioxy)phenyl]aminocarbonyl}thiophene-3-sulfonamide Carbonyidiimidazole (553 mg, 3.41 mmol) was added to a solution of <strong>[184040-74-2]N-(4-chloro-3-methyl-5-isoxazolyl)-2-carboxylthiophene-3-sulfonamide</strong> (1.0 g, 3.1 mmol) in dry DMF (10 ml). The mixture was stirred at room temperature for 15 minutes to give mixture (I). NaH (60% dispersion in mineral oil, 521 mg, 13.02 mmol) was added to a solution of 2'-amino-4',5'-(methylenedioxy)acetophenone (1.13 g, 6.2 mmol) in dry DMF (10 ml) at 0 C. The mixture was stirred at 0 C. for 15 minutes to give mixture (II). Mixture (I) was slowly cannulated into mixture (II) at 0 C. The resulting mixture was stirred at 0 C. for 4 hours. The reaction mixture was poured into 2N HCl (aq., 200 ml) and the resulting precipitate was filtered. The solid was washed with water (2*10 ml) and ethyl ether (2*10 ml) to give N-(4-chloro-3-methyl-5- isoxazolyl)2-[2-acetyl-4,5-(methylenedioxy)phenyl]aminocarbonyl}thiophene-3-sulfonamide (730 mg, 49% yield) as a dull yellow powder, m.p. 191-193 C. |
49% | With NaH; 1,1'-carbonyldiimidazole; In N,N-dimethyl-formamide; mineral oil; | EXAMPLE 148 N-(4-chloro-3-methyl-5-isoxazolyl)2-[2-acetyl-4,5-(methylenedioxy)phenyl]aminocarbonyl}thiophene-3-sulfonamide Carbonyldiimidazole (553 mg, 3.41 mmol) was added to a solution of <strong>[184040-74-2]N-(4-chloro-3-methyl-5-isoxazolyl)-2-carboxylthiophene-3-sulfonamide</strong> (1.0 g, 3.1 mmol) in dry DMF (10 ml). The mixture was stirred at room temperature for 15 minutes to give mixture (I). NaH (60% dispersion in mineral oil, 521 mg, 13.02 mmol) was added to a solution of 2'-amino-4',5'-(methylenedioxy)acetophenone (1.13 g, 6.2 mmol) in dry DMF (10 ml) at 0 C. The mixture was stirred at 0 C. for 15 minutes to give mixture (II). Mixture (I) was slowly cannulated into mixture (II) at 0 C. The resulting mixture was stirred at 0 C. for 4 hours. The reaction mixture was poured into 2N HCl (aq., 200 ml) and the resulting precipitate was filtered. The solid was washed with water (2*10 ml) and ethyl ether (2*10 ml) to give N-(4-chloro-3-methyl-5-isoxazolyl)2-[2-acetyl-4,5-(methylenedioxy)phenyl]aminocarbonyl}thiophene-3-sulfonamide (730 mg, 49% yield) as a dull yellow powder, m.p. 191-193 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
19% | With NaH; 1,1'-carbonyldiimidazole; In tetrahydrofuran; water; mineral oil; | EXAMPLE 106 N-(4-chloro-3-methyl-5-isoxazolyl)-2-{1-cyano-1-[(3,4-methylenedioxy)phenyl]acetyl}thiophene-3-sulfonamide Carbonyldiimidazole (603 mg, 3.72 mmol) was added to a solution of N-(4-chloro-3-methyl-5-isoxazolyl)-2-carboxylthiophene-3-sulfonamide (Example 17) (1.0g, 3.1 mmol) in dry THF (40 ml). The mixture (I) was stirred at room temperature for 15 minutes. NaH (868 mg, 60% in mineral oil, 21.7 mmol) was added to a solution of (3,4-methylenedioxy)phenylacetonitrile in THF (100 ml). The mixture (11) was refluxed for 30 minutes and then allowed to warm to room temperature. The mixture (I) was then cannulated into mixture (11) while cooled by ice-bath and the resulting mixture was allowed to warm to room temperature. Water was added to quench excess NaH. THF was then stripped off on a rotavap. The residue was partitioned between 1N NaOH and Et2 O. The aqueous layer was acidified with concentrated HCl with cooling to pH ~1 and extracted with EtOAc. The organic layer was dried (MgSO4), the solid filtered and the filtrate concentrated. The residue was purified by HPLC to give N-(4-chloro-3-methyl-5-isoxazolyl)-2-{1-cyano-1-[3,4-(methylenedioxy)phenyl]acetyl}thiophene-3-sulfonamide (277 mg, 19% yield) as a yellowish powder, m.p. 142-142 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | To a mixture of 3-<strong>[184040-74-2][(4-chloro-3-methyl-1,2-oxazol-5-yl)sulfamoyl]thiophene-2-carboxylic acid</strong> (2.5 g, 7.8 mmol) described in Production Example 1-1 and tetrahydrofuran (25 mL) was added 1,1′-carbonyldiimidazole (2.0 g, 12 mmol) at room temperature, followed by stirring at that temperature for 30 minutes. Imidazole (1.1 g, 16 mmol) and N,O-dimethylhydroxylamine hydrochloride (1.2 g, 12 mmol) were added successively at room temperature to the reaction mixture, followed by stirring at that temperature for 5 hours. A 1 N aqueous solution of hydrochloric acid (50 mL) was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate, and the solvent was distilled away under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=9:1) to give the title compound (1.5 g, 53% yield). 1H-NMR Spectrum (CDCl3) δ (ppm): 2.23 (3H, s), 3.45 (3H., s), 3.74 (3H, s), 7.47 (1H, d, J=5.3 Hz), 7.53 (1H, d, J=5.3 Hz). | |
Step 5 2-[2-(6-Methyl-benzo[1,3]dioxol-5-yl)-acetyl]-thiophene-3-sulfonic acid (4-chloro-3-methyl-isoxazol-5-yl)-amide: 1,1'-carbonyldiimidazole (600 mg) was added to a solution of 3-[(4-chloro-3-methyl-5-isoxazolyl)sulfamoyl]-2-thiophenecarboxylic acid (900 mg, 2.79 mmol) in anhydrous tetrahydrofuran (20 mL). The mixture was stirred at ambient temperature for about 15 minutes and then sequentially treated with imidazole (380 mg, 5.58 mmol) and N,O-dimethylhydroxylamine hydrochloride (420 mg, 4.3 mmol). Under continuous stirring, the mixture was maintained at ambient temperature for about 4 hours. The solvent was removed in vacuo and the residue was partitioned between ethyl acetate (100 mL) and 1 N hydrochloric acid (30 mL). The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated. The resulting residue was treated with toluene and re-concentrated. The resulting red oil was dissolved in anhydrous tetrahydrofuran (20 mL), cooled to about 0 C., and then treated with a Grignard reagent prepared from 5-chloromethyl-6-methyl-benzo[1,3]dioxole (800 mg, 4.36 mmol) and magnesium turnings (826 mg, 34.4 mmol) in tetrahydrofuran (50 mL). Under continuous stirring, the mixture was maintained at about 0 C. for about 1 hour and then at ambient temperature for about 2 hours. At about 0 C., the reaction mixture was quenched with a mixture of concentrated hydrochloric acid (20 mL) and methanol (50 mL). The mixture was stirred at about 0 C. for about 10 minutes, and then concentrated in vacuo. The aqueous residue was partitioned between ethyl acetate (100 mL) and 1 N hydrochloric acid (30 mL). The crude product was isolated using standard extractive work up and purified by prep-TLC (eluted with CH2Cl2:MeOH=7:1) to give 2-[2-(6-methyl-benzo[1,3]dioxol-5-yl)-acetyl]-thiophene-3-sulfonic acid (4-chloro-3-methyl-isoxazol-5-yl) amide (150 mg, 30%) as a yellow solid. 1H NMR (300 MHz, CD3OD) δ 7.77 (d, J=5.1 Hz, 1H), 7.40 (d, J=5.1 Hz, 1H), 6.74 (d, J=4.2 Hz, 2H), 5.94 (s, 3H), 4.76 (s, 2H), 2.04 (s, 3H), 1.99 (s, 3H); ESI-MS: m/z=455 (MH)+; HPLC purity: 95%. 1,1'-carbonyldiimidazole (250 mg) was added to a solution of 3-[(4-chloro-3-methyl-5-isoxazolyl)sulfamoyl]-2-thiophenecarboxylic acid (400 mg, 10.1 mmol) in anhydrous tetrahydrofuran (20 mL). The resulting mixture was stirred at ambient temperature for about 15 minutes and then sequentially treated with imidazole (168 mg, 2.5 mmol) and N,O-dimethylhydroxylamine hydrochloride (184 mg, 1.89 mmol). Under continuous stirring, the mixture was maintained at ambient temperature for about 4 hours. The solvent was removed in vacuo and the residue was partitioned between ethyl acetate (100 mL) and 1 N hydrochloric acid (30 mL). The organic layer was extracted, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was treated with toluene (30 mL) and re-concentrated. The resulting red oil was dissolved in anhydrous tetrahydrofuran (20 mL), cooled to about 0 C. in an ice-bath, and treated with a Grignard reagent prepared from d2-5-chloromethyl-6-methyl-benzo[1,3]dioxole (800 mg, 4.29 mmol) and magnesium turnings (826 mg, 34.4 mmol) in tetrahydrofuran (50 mL). Under continuous stirring, the mixture was maintained at about 0 C. for about 1 hour and then at ambient temperature for about 2 hours. At about 0 C., the reaction mixture was quenched with a mixture of concentrated hydrochloric acid (20 mL) and methanol (50 mL). After continuous stirring at about 0 C. for about 10 minutes, the reaction mixture was concentrated in vacuo. The aqueous residue was partitioned between ethyl acetate (100 mL) and 1 N hydrochloric acid (30 mL). The crude product was isolated using standard extractive work up and purified by prep-TLC (eluted with CH2Cl2:MeOH=7:1) to give d2-2-[2-(6-methyl-benzo[1,3]dioxol-5-yl)-acetyl]-thiophene-3-sulfonic acid (4-chloro-3-methyl-isoxazol-5-yl) amide (120 mg, 24%) as a yellow solid. 1H NMR (300 MHz, CD3OD) δ 7.75 (d, J=5.1 Hz, 1H), 7.40 (d, J=5.1 Hz, 1H), 6.72 (d, J=3.9 Hz, 2H), 4.76 (s, 2H), 2.04 (s, 3H), 1.99 (s, 3H); ESI-MS: m/z=457 (MH)+; HPLC purity: 95%. |
Tags: 184040-74-2 synthesis path| 184040-74-2 SDS| 184040-74-2 COA| 184040-74-2 purity| 184040-74-2 application| 184040-74-2 NMR| 184040-74-2 COA| 184040-74-2 structure
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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. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
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. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
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: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
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 |
Sorry,this product has been discontinued.
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