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Chemical Structure| 7151-76-0 Chemical Structure| 7151-76-0

Structure of 7151-76-0

Chemical Structure| 7151-76-0

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Product Details of [ 7151-76-0 ]

CAS No. :7151-76-0
Formula : C8H9NO4S
M.W : 215.23
SMILES Code : O=C(O)C1=CC=C(NS(=O)(C)=O)C=C1
MDL No. :MFCD00025052
InChI Key :SROHFTOYGFCJAF-UHFFFAOYSA-N
Pubchem ID :250653

Safety of [ 7151-76-0 ]

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

Application In Synthesis of [ 7151-76-0 ]

* 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 [ 7151-76-0 ]

[ 7151-76-0 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 7151-76-0 ]
  • [ 126377-18-2 ]
  • [ 126377-23-9 ]
  • 2
  • [ 7151-76-0 ]
  • [ 137898-68-1 ]
  • [ 138490-68-3 ]
  • 3
  • [ 7151-76-0 ]
  • [ 138490-83-2 ]
  • [ 138490-76-3 ]
  • 4
  • [ 7151-76-0 ]
  • [ 138490-80-9 ]
  • [ 138490-64-9 ]
  • 5
  • [ 7151-76-0 ]
  • [ 658-78-6 ]
  • [ 14001-51-5 ]
  • 6
  • [ 7151-76-0 ]
  • [ 100643-71-8 ]
  • N-{4-[4-(8-Chloro-5,6-dihydro-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-piperidine-1-carbonyl]-phenyl}-methanesulfonamide [ No CAS ]
  • 7
  • [ 50790-28-8 ]
  • [ 7151-76-0 ]
  • 8
  • [ 7151-76-0 ]
  • (±)-trans-3-amino-1-benzyloxycarbonyl-4-hydroxypyrrolidine [ No CAS ]
  • (3R,4R)-3-Hydroxy-4-(4-methanesulfonylamino-benzoylamino)-pyrrolidine-1-carboxylic acid benzyl ester [ No CAS ]
  • (3R,4R)-3-(4-Methanesulfonylmethyl-benzoylamino)-4-(4-methanesulfonylmethyl-benzoyloxy)-pyrrolidine-1-carboxylic acid benzyl ester [ No CAS ]
  • 11
  • [ 150-13-0 ]
  • [ 124-63-0 ]
  • [ 7151-76-0 ]
YieldReaction ConditionsOperation in experiment
Example 15 4-[1-Dodecanoyloxy-2-N-(4-carboxyphenyl)sulfonamido]ethyl-5-hydroxy-2(5H)-furanone (Compound 13) 4-Aminobenzoic acid is reacted with methanesulfonyl chloride (Compound 19) to give N-(4-carboxyphenyl)methanesulfonamide.
  • 12
  • [ 7151-76-0 ]
  • trans-3-(4-methanesulfonamidobenzamido)-4-[4-(2-carboxy-6-hydroxybenzoyl)-3,5-dihydroxybenzoyloxy]pyrrolidine trifluoroacetate [ No CAS ]
  • 13
  • [ 7151-76-0 ]
  • (3R,4R)-3-[3,5-Bis-benzyloxy-4-(2-benzyloxy-6-benzyloxycarbonyl-benzoyl)-benzoyloxy]-4-(4-methanesulfonylamino-benzoylamino)-pyrrolidine-1-carboxylic acid benzyl ester [ No CAS ]
  • 14
  • [ 619-45-4 ]
  • [ 7151-76-0 ]
  • 15
  • [ 124-63-0 ]
  • [ 94-09-7 ]
  • [ 7151-76-0 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In methanol; dichloromethane; (a) 4-Methanesulfonylamino-benzoic acid. Ethyl 4-amino-benzoate (5 g, 30 mmol, 1.0 equiv) was mixed in 50 mL of CH2Cl2 with Et3N (6.1 g, 60 mmol, 2.0 equiv). The solution was cooled to 0 C. and methanesulfonyl chloride (3.8 g, 33 mmol. 1.1 equiv) was added as a solution in 15 mL of CH2Cl2 dropwise over a 15 min period. The reaction was stirred for 4 h at which time it was diluted with 50 mL of water. Layers were separated and the organic layer was washed with 50 mL of saturated sodium bicarbonate solution and concentrated. The resulting ester was dissolved in 50 mL of MeOH and treated with 50 mL of 5 N NaOH for 4 h. The reaction solution was extracted with Et2O and the aqueous layer was acidified to give a white precipitate that was collected by filtration. The solid was dried and used without further purification.
With pyridine; In dichloromethane; Preparation 1 4-[(Methylsulfonyl)amino]benzoic acid To 215.2 g (2.72 mole) of pyridine in 1250 ml of dichloromethane is added 238 g (1.44 mole) of ethyl 4-aminobenzoate. After cooling to 0 C., a solution of 177.6 g (1.55 mole) of methanesulfonyl chloride in 250 ml of dichloromethane is added with stirring. Upon completion of the addition, the ice bath is removed and the reaction is stirred for one hour at room temperature. The reaction mixture is extracted with 3*500 ml of 4N sodium hydroxide and the aqueous extract is first washed with 3*500 ml of dichloromethane and then with 3*250 ml of ether. The aqueous extract is refluxed for two hours and allowed to cool overnight. The reaction is acidified with concentrated hydrochloric acid until a white precipitate forms. Collection by filtration followed by drying provides 310 g of the title compound. NMR (DMSO-d6): delta=3.2(s,3), 7.25-7.55(m,2) and 7.85-8.20 (m,2)ppm.
  • 16
  • [ 148672-79-1 ]
  • [ 7151-76-0 ]
  • [ 530-62-1 ]
  • N-(1-Azabicyclo[3.3.1non-5-ylmethyl)-4-[(methylsulfonyl)aminol]benzamide [ No CAS ]
  • sesquihydrate [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.61 g (32%) In tetrahydrofuran; N-methyl-acetamide; methanol; acetonitrile; EXAMPLE 9 N-(1-Azabicyclo[3.3.1non-5-ylmethyl)-4-[(methylsulfonyl)aminol]benzamide A solution/suspension of 4-[(methanesulfonyl)amino]benzoic acid (1.08 g, 5.0 mmol) in anhydrous 1:1 tetrahydrofuran/dimethylformamide (4 mL) was treated with 1,1'-carbonyldiimidazole (0.89 g, 5.5 mmol), stirred for one hour, then degassed over 15 minutes under a stream of nitrogen. A solution of 1-azabicyclo[3.3.1]nonane-5-methanamine (0.85 g, 5.5 mmol) in anhydrous tetrahydrofuran (4 mL) was added, and the mixture was stirred at room temperature for 18 hours and at 50 C. for three hours, then concentrated in vacuo. The residue was triturated from acetonitrile/ether, then dissolved in 3.2 tetrahydrofuran/methanol and filtered through a short column of alumina (eluted with 3:2 tetrahydrofuran/methanol). The filtrate was concentrated in vacuo and recrystallized (2 crops) from 2-propanol/ether to afford 0.61 g (32%) of the sesquihydrate of the title compound as a voluminous colorless solid; mp 137-139 C. (foam). Analysis: Calc. for C17 H25 N3 O3 S.1.5H2 O: C, 53.95; H, 7.46; N, 11.10. Found: C, 54.14; H, 7.35; N, 10.49.
  • 17
  • [ 7151-77-1 ]
  • [ 7151-76-0 ]
YieldReaction ConditionsOperation in experiment
1.4 g (65%) In sodium hydroxide; EXAMPLE 16 STR20 4-[(Methylsulfonyl)amino]benzoic acid. A mixture of ethyl 4-[(methylsulfonyl)amino]benzoate (Lumma, W. C. et al. J. Med. Chem. 1987, 30, 758-763) (2.43 g, 0.01 mol) in 1N sodium hydroxide (22 mL, 0.022 mol) was stirred at room temperature for 24 h and then at 48 C. for 24 h. The mixture was acidified with concentrated hydrochloric acid to give a white precipitate which was separated by filtration. The cake was washed with water, dried, and recrystallized with ethanol-water to give 1.4 g (65%) of the title compound as white flakes, mp 248 C. Analysis: Calculated for C8 H9 NO4 S: C, 44.64; H, 4.21; N, 6.50 Found: C, 44.71; H, 4.26; N, 6.50
  • 18
  • [ 7151-76-0 ]
  • 4-[(methylsulfonyl)amino]benzoic acid sodium salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In water; Preparation 2 4-[(Methylsulfonyl)amino]benzoic acid sodium salt To 500 ml of water is added 63.4 g (1.59 mole) of sodium hydroxide and the mixture is stirred until all the solid has dissolved. To this is slowly added 310 g (1.44 mole) of <strong>[7151-76-0]4-[(methylsulfonyl)amino]benzoic acid</strong>. The reaction is stirred for 15 minutes at ambient temperature after all the solid has dissolved. After removal of the water in vacuo, the residue is triturated with isopropyl alcohol, evaporated, triturated with acetone and concentrated in vacuo. The solid is dried under vacuum for 72 hours to provide 333.7 g of the title compound. NMR (DMSO-d6): delta=3.0(s,3), 5.3-5.8(br s,2), 7.0-7.3 (m,2) and 7.8-8.1(m,2)ppm.
  • 19
  • [ 7151-76-0 ]
  • [ 63421-72-7 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride; for 2h;Heating; A mixture of 2-chlorobenzoic acid (1b) (0.61 g, 3.92 mmol) and thionyl chloride (1 mL) was heated for 2 h. The excess of thionyl chloride was recovered under reduced pressure and the residue so obtained was dissolved in dry dioxane (1 mL). The solution was then dropwise added to mixture of 2-amino-4,5-dimethoxybenzamide (2) (0.7 g, 3.57 mmol) and TEA (1.2 mL, 8.92 mmol) in dry dioxane (2 mL) at 10 C. The reaction mixture was stirred at rt for another 1 h and quenched into cold water (50 mL). The precipitate formed was filtered, washed with water and dried to obtain compound 3b (0.85 g, 71%): mp 213-215 C (dec.); IR (KBr,): 3406, 3305, 1658, 1645, 1612, 1525, 1253, 1078 and 1039 cm-1.
  • 20
  • [ 619-45-4 ]
  • [ 7143-01-3 ]
  • [ 7151-76-0 ]
  • 21
  • C24H41N6O4Pol [ No CAS ]
  • [ 7151-76-0 ]
  • C32H48N7O7PolS [ No CAS ]
  • 22
  • [ 1218935-62-6 ]
  • [ 7151-76-0 ]
  • [ 1218934-92-9 ]
YieldReaction ConditionsOperation in experiment
27% A reaction vial was charged with (R)-6-(2-(2,5-difluorophenyl)pyrrolidin-l- yl)imidazo[l,2-b]pyridazin-3 -amine (Preparation B; 30 mg, 0.095 mmol), 4- (methylsulfonamido)benzoic acid (41 mg, 0.19 mmol), and 2(lH-azabenzotriazol-l-yl)- 1,1,3,3-tetramethyl uranium hexafluorophophate methanaminium (HATU; 72 mg, 0.19 mmol). DMF (0.8 mL) was added to the mixture to make a solution. The reaction mixture was cooled in an ice bath for 10 minutes before DIEA (0.05 mL, 0.29 mmol) was added dropwise. After addition, reaction was warmed to ambient temperature and stirred overnight. The reaction mixture was diluted with EtOAc (20 mL), washed with water and brine (10 mL each), and concentrated. The crude material was purified by reverse-phase column chromatography, eluting with 5 to 60% acetonitrile/water to yield (R)-N-(6-(2-(2,5- difluorophenyl)pyrrolidin- 1 -yl)imidazo [ 1 ,2-b]pyridazin-3 -yl)-4-(methylsulfonamido)benzamide as a yellowish solid (13 mg, 27% yield). MS (apci negative) m/z = 511.4 (M-H).
  • 23
  • [ 7151-76-0 ]
  • [ 1357294-65-5 ]
  • 24
  • [ 7151-76-0 ]
  • [ 1357294-90-6 ]
  • 25
  • [ 1333425-31-2 ]
  • [ 7151-76-0 ]
  • [ 1333426-76-8 ]
  • 26
  • [ 23903-46-0 ]
  • [ 7151-76-0 ]
  • [ 1429226-60-7 ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; for 24h; General procedure: To a solution of acid (1.0 eq), HOBt (1.5 eq), EDCI (1.5 eq) and triethylamine (1.5 eq) in DMF, compound a was added and the mixture was stirred for 24h. The mixture was poured into saturated NaHCO3 solution, extracted by ethyl acetate three times and the combined organic layer was washed with water and brine, and dried over with anhydrous Na2SO4. The concentrated residue was purified by recrystallization directly from CHCl3/MeOH or purified by flash column chromatography on silica gel to give the pure products.
  • 27
  • [ 7151-76-0 ]
  • [ 1548871-29-9 ]
  • 28
  • [ 7151-76-0 ]
  • [ 1548871-37-9 ]
  • 29
  • [ 7151-76-0 ]
  • [ 1548869-60-8 ]
  • 30
  • [ 7151-76-0 ]
  • [ 100-39-0 ]
  • [ 1548871-14-2 ]
  • 31
  • [ 7151-76-0 ]
  • [ 100-39-0 ]
  • [ 1548871-24-4 ]
  • 32
  • [ 7151-76-0 ]
  • tert-butyl [trans-2-(4-aminophenyl)cyclopropyl](cyclopropylmethyl)carbamate [ No CAS ]
  • N-(4-{trans-2-[(cyclopropylmethyl)amino]cyclopropyl}phenyl)-4-[(methylsulfonyl)amino]benzamide hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 135 N-(4-{trans-2-[(cyclopropylmethyl)amino]cyclopropyl}phenyl)-4-[(methylsulfonyl)amino]benzamide hydrochloride By a method similar to Example 80, the title compound (81.1 mg) was obtained from tert-butyl [trans-2-(4-aminophenyl)cyclopropyl](cyclopropylmethyl)carbamate (96.9 mg) and <strong>[7151-76-0]4-(methanesulfonamido)benzoic acid</strong> (83 mg). MS (API+): [M+H]+ 400.3. 1H NMR (300 MHz, DMSO-d6) delta 0.32-0.40 (2H, m), 0.53-0.62 (2H, m), 0.97-1.12 (1H, m), 1.21-1.33 (1H, m), 1.41-1.53 (1H, m), 2.36-2.46 (1H, m), 2.82-3.01 (3H, m), 3.09 (3H, s), 7.15 (2H, d, J = 8.7 Hz), 7.30 (2H, d, J = 8.9 Hz), 7.69 (2H, d, J = 8.7 Hz), 7.93 (2H, d, J = 8.9 Hz), 9.08 (2H, brs), 10.14 (2H, s).
  • 33
  • [ 7151-76-0 ]
  • [ 91918-90-0 ]
  • N-(4-(2-(6-methyl-[1,3]dioxolo[4,5-g]quinolin-8-yl)hydrazine-1-carbonyl)phenyl)methanesulfonamide [ No CAS ]
  • 34
  • [ 7151-76-0 ]
  • 20'-aminovinblastine [ No CAS ]
  • C54H66N6O11S [ No CAS ]
  • 35
  • [ 7151-76-0 ]
  • 2-phenyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4(3H)-one dihydrochloride [ No CAS ]
  • N-{4-[(4-oxo-2-phenyl-3,5,7,8-tetrahydropyrido[4,3-d]pyrimidin-6(4H)-yl)carbonyl]phenyl}methanesulfonamide [ No CAS ]
 

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