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Structure of 121-60-8
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 121-60-8 |
Formula : | C8H8ClNO3S |
M.W : | 233.67 |
SMILES Code : | O=S(C1=CC=C(NC(C)=O)C=C1)(Cl)=O |
MDL No. : | MFCD00007442 |
InChI Key : | GRDXCFKBQWDAJH-UHFFFAOYSA-N |
Pubchem ID : | 8481 |
GHS Pictogram: |
![]() ![]() |
Signal Word: | Danger |
Hazard Statements: | H314-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338-P310 |
Class: | 8 |
UN#: | 3261 |
Packing Group: | Ⅱ |
* 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 |
---|---|---|
59% | at 20℃; for 12 h; | A mixture of 4-acetamidobenzene-1-sulfonyl chloride (4.27 mmol), 5-methylisoxazol-3-amine (4.49 mmol) and DMAP (0.21 mmol) in anhydrous pyridine (10 mL) was stirred at room temperature for 12 h. After completion of reaction, solvent was evaporated to dryness and diluted with water and extracted with ethyl acetate. The combined organic layers were washed with water and 1 M aqueous HCl, dried over anhydrous Na2SO4, filtered, and concentrated under vacuum. The solid residue obtained was purified with flash column chromatography using heptanes to EtOAc (50-100percent) gradient elution to afford the compound 2. 4.2.1 N-(4-(N-(5-Methylisoxazol-3-yl)sulfamoyl)phenyl)acetamide (2) Yield: 59percent; ESIMS m/z calcd for C12H13N3O4S [M + H]+, 296.07; found 296.06; 1H NMR (400 MHz, (CD3)2SO): δ 11.30 (bs, 1H), 10.35 (bs, 1H), 7.79-7.73 (m, 4H), 6.12 (s, 1H), 2.29 (s, 3H), 2.07 (s, 3H). 13C (100 MHz, (CD3)2SO): δ 170.71, 169.57, 158.07, 144.01, 133.36, 128.50, 119.15, 95.84, 24.57, 12.48. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; In ethanol; ethyl acetate; acetonitrile; | The starting 4-(N,N-dimethylaminosulfonyl)aniline was prepared as follows. To a suspension of p-acetamidobenzenesulfonyl chloride (2.0 g) in dry acetonitrile (15 ml) at 22 C. was added 40% aqueous dimethylamine (30 ml), and the mixture was stirred for 18 hours. The reaction mixture was concentrated and partitioned between ethyl acetate and water. The ethyl acetate was washed with brine, dried (Na2 S4), and evaporated under reduced pressure to give a colourless crystalline solid (1.17 g). This was dissolved in ethanol and the resultant solution was treated with concentrated hydrochloric acid and heated to reflux. The reaction mixture was then cooled to 22 C. and adjusted to pH 8 with concentrated NH4 OH. The resultant suspension was cooled, filtered, the solvent washed with water and dried to give a light tan solid (0.88 g); MS: m/z=201(M+1); NMR: 2.50 (s,6), 6.04 (broad s,2), 6.65 (d,2), 7.35 (d,2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; calcium carbonate; In ice-water; water; | EXAMPLE 94 730 ml of water and 159 g of Na2 SO3 (95percent strength by weight) were introduced first. 530 g of 4-acetylaminobenzenesulfonyl chloride were then added a little at a time with stirring at 70° C., while the pH was maintained at about 9 with 95 ml of 50percent strength by weight sodium hydroxide solution. After 3 hours of subsequent stirring at 70° C., insolubles were filtered off, 250 g of ice were added at 30° C., and 375 ml of 17percent strength by weight hydrochloric acid were added with stirring at pH 1.0 to bring down a precipitate, while the temperature was maintained at <=10° C. The resulting suspension was filtered with suction after 1.5 hours and the filter residue was washed with 1.5 1 of ice-water. The filter material was then suspended in 400 ml of ice-water and dissolved at about 15° C. with 74 ml of 30percent strength by weight sodium hydroxide solution at pH 9.0. This gave 782 ml of a clear solution containing 185 g of the sodium salt of 4-acetylaminobenzenesulfinic acid. 654 ml of this solution (corresponding to 154.7 g of the sodium salt of 4-acetylaminobenzenesulfinic acid) were introduced first, and 365 g of 50percent strength by weight 2-nitrochlorobenzene-4-sulfonic acid were added with stirring at pH 6.2. The pH was then adjusted to 7.0 with a few drops of sodium hydroxide solution. 9 g of CaCO3 and 0.35 g of copper powder were added, and the mixture was stirred at 100° C. for 20 hours and then filtered hot. The resulting solution was admixed with 180 ml of 17percent strength by weight hydrochloric acid and refluxed for 4 hours. The suspension obtained was then filtered with suction at room temperature, and the filter residue was washed with 2 1 of ice-water and dried at 70° C. under reduced pressure. Yield: 250 g of 4-amino-2'-nitro-4'-sulfodiphenyl sulfone of the formula STR179 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hexamethyldisilazane; In pyridine; N,N-dimethyl-formamide; | N-(4-{6-[7-(2,2-Dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-1-methyl-1H-indol-4-ylsulfamoyl}-phenyl)-acetamide. Substituting N-[4-(6-bromo-1-methyl-1H-indol-4-ylsulfamoyl)-phenyl]-acetamide (prepared by treatment of <strong>[350800-81-6]6-bromo-1H-indol-4-ylamine</strong> first with sodium hexamethyldisilazide and iodomethane in N,N-dimethylformamide, then with 4-acetylamino-benzenesulfonyl chloride in pyridine) for 6-bromo-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one. MP=275-276 C, (M+H)+=545. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; sodium hexamethyldisilazane; In pyridine; N,N-dimethyl-formamide; | 4-Amino-N-{6-[7-(2,2-dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-1-methyl-1H-indol-4-yl}-benzenesulfonamide. Substituting N-[4-(6-bromo-1-methyl-1H-indol-4-ylsulfamoyl)-phenyl]-acetamide (prepared by treatment of <strong>[350800-81-6]6-bromo-1H-indol-4-ylamine</strong> first with sodium hexamethyldisilazide and iodomethane in N,N-dimethylformamide, then with 4-acetylamino-benzenesulfonyl chloride in pyridine) for 6-bromo-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one. Followed by treatment with aqueous sodium hydroxide. MP=243-245 C, (M+H)+=503. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
N-(4-{6-[7-(2,2-Dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-1-methyl-1H-indol-4-ylsulfamoyl}-phenyl)-acetamide. Substituting N-[4-(6-bromo-1-methyl-1H-indol-4-ylsulfamoyl)-phenyl]-acetamide (prepared by treatment of <strong>[350800-81-6]6-bromo-1H-indol-4-ylamine</strong> first with sodium hexamethyldisilazide and iodomethane in N,N-dimethylformamide, then with 4-acetylamino-benzenesulfonyl chloride in pyridine) for 6-bromo-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one. MP=275-276 C, (M+H)+=545. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; | N-(4-{6-[7-(2,2-Dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-2,3-dihydrobenzo[1,4]oxazine-4-sulfonyl}-phenyl)-acetamide. Substituting N-[4-(6-bromo-2,3-dihydro-benzo[1,4]oxazine-4-sulfonyl)-phenyl]-acetamide (prepared by treatment of <strong>[105655-01-4]6-bromo-3,4-dihydro-2H-benzo[1,4]oxazine</strong>(Bioorg. Med. Chem., 15 (2007), 5912) with 4-acetylamino-benzenesulfonyl chloride in pyridine) for 6-bromo-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one. MP=273-274 C, (M+H)+=534. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | General procedure: To a solution of p-acetamidobenzenesulfonyl chloride (275 mg, 1.18 mmol) in pyridine (5 mL) was added ethyl 2-(5-amino-1,3,4-thiadiazol-2-yl)acetate (200 mg, 1.07 mmol). The reaction mixture was stirred at rt for 4.5 h, then 2 M HCl (10 mL) was added and the mixture extracted with EtOAc (3 ' 50 mL). The organic extracts were washed with water (20 mL), brine (20 mL), dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The residue was subjected to chromatography on silica gel (70-230 mesh) eluted with CH2Cl2:MeOH 19:1, affording the product 13 (312 mg, 0.81 mmol, 76percent yield), | |
73% | With pyridine; at 20℃; for 4.5h; | To a solution of /?-acetamidobenzenesulfonyl chloride (1.98 g, 8.47 mmol) in pyridine (20 rnL) was added ethyl 5-amino-l,3,4-thiadiazole-2-carboxylate (1.2 g, 7.06 mmol). The reaction mixture was stirred at room temperature for 4.5 h, than 2 M HCl (50 mL) was added to quench the reaction. The mixture was extracted with ethyl acetate (3 x 60 mL). The organic extracts were washed with water (50 mL), brine (50 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by chromatography on silica gel (70-230 mesh) eluted with CH2Cl2 methanol 19:1 to give the product as a solid, mp 201-202 0C, in 73percent yield (1.91 g, 5.15 mmol); 1H NMR (300 MHz, DMSO-^) delta 1.29 (t, 3H, J = 6.9 Hz), 2.08 (s, 3H), 4.37 (q, 2H, J = 7.8 Hz), 7.74 (m, 4H), 10.32 (s, IH); 13C NMR (75 MHz, OMSO-d6) delta 13.9, 14.0, 24.1, 62.9, 118.6, 127.1, 134.9, 143.2, 147.2, 157.5, 167.6, 169.0; MS (LCQ, ESI+) Calcd for Ci3Hi5N4O5S2 371.0, found 371.0 (M+H)+; HRMS (ESI+, m/z) Calcd for Ci3Hi5N4O5S2 371.0484, found 371.0472 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | In tetrahydrofuran; | Preparation 174-Amino-N,N-dimethyl-benzenesulfonamideDissolve 4-acetamidobenzene-l-sulfonyl chloride (1.13 g, 4.84 mmol) in THF (20 mL). Add dimethylamine (2 M in THF, 10 mL, 20.00 mmol) slowly with stirring. Stir the mixture overnight. Concentrate the mixture under reduced pressure. Dissolve the residue in EtOAc (50 mL). Wash the organic portion with 2 N NaOH and brine. Dry over a2S04; filter; collect the filtrate; and concentrate to dryness. Dissolve the resulting oil in ethanol. Add concentrated hydrochloric acid (10 mL, 116.43 mmol). Heat the mixture to reflux and stir 4 h. Concentrate the material under reduced pressure. Dissolve the residue in EtOAc (50 mL) and water (50 mL). Adjust to about pH = 10 with 2 N NaOH. Wash the organic layer with brine; dry over a2S04; filter; collect the filtrate; X-19317-20- and concentrate the filtrate to dryness to afford the title compound (0.85 g, 88%). LC- ES/MS m/z 201 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25% | In dichloromethane; at 20℃; for 3h; | To a suspension of <strong>[658-27-5]3-fluorophenyl hydrazine</strong> (302.7 mg, 2.4 mmol) in CH2Cl2 (1.2 mL) was added 4-(acetylamino)benzenesulfonyl chloride (280.4 mg, 1.2 mmol). The reaction was stirred at room temperature for 3 h. After the reaction was completed, MeOH was added and the solution was concentrated under reduced pressure. The purification was carried out by Isco CombiFlash Companion column chromatography (silica gel, 0-30 % MeOH in CH2Cl2) to give N-(4-[2-(3-fluorophenyl)hydrazinyl]sulfonyl}phenyl)acetamide (97.0 mg, 25 %) as a powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With Mg-Al hydrotalcite; In acetone; for 3.25h;Sonication; Green chemistry; | General procedure: A solution of the heterocyclic amine (1 mmol) in acetone (1.5 mL) was added into a 10mL round flask containing Mg-Al hydrotalcite (0.8 mmol, 0.48 g) and p-acetamidobenzenesulfonyl chloride (2 mmol, 0.467 g). The flask was placed into an ultrasound bath where the mixture of reactants was exposed to ultrasound irradiation for a specific period of time (Method D, Table 3). After reaction completion, the reaction mixture was worked up as described for Method A. |
Tags: 121-60-8 synthesis path| 121-60-8 SDS| 121-60-8 COA| 121-60-8 purity| 121-60-8 application| 121-60-8 NMR| 121-60-8 COA| 121-60-8 structure
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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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The concentration of the dissolution solution you need to prepare is mg/mL