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Chemical Structure| 1103234-56-5
Chemical Structure| 1103234-56-5
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Product Details of [ 1103234-56-5 ]

CAS No. :1103234-56-5 MDL No. :MFCD18157658
Formula : C10H11F2NO4S Boiling Point : -
Linear Structure Formula :- InChI Key :RTAWCKGXCGSFJI-UHFFFAOYSA-N
M.W : 279.26 Pubchem ID :46192923
Synonyms :

Calculated chemistry of [ 1103234-56-5 ]

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 5
Num. H-bond acceptors : 6.0
Num. H-bond donors : 2.0
Molar Refractivity : 61.2
TPSA : 91.85 Ų

Pharmacokinetics

GI absorption : High
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) : -6.93 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.66
Log Po/w (XLOGP3) : 1.51
Log Po/w (WLOGP) : 3.55
Log Po/w (MLOGP) : 0.62
Log Po/w (SILICOS-IT) : 1.4
Consensus Log Po/w : 1.55

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.44
Solubility : 1.02 mg/ml ; 0.00364 mol/l
Class : Soluble
Log S (Ali) : -3.05
Solubility : 0.251 mg/ml ; 0.000897 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.5
Solubility : 0.0881 mg/ml ; 0.000316 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.36

Safety of [ 1103234-56-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1103234-56-5 ]

* 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.

  • Upstream synthesis route of [ 1103234-56-5 ]
  • Downstream synthetic route of [ 1103234-56-5 ]

[ 1103234-56-5 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 1103234-56-5 ]
  • [ 183208-35-7 ]
  • [ 918504-27-5 ]
YieldReaction ConditionsOperation in experiment
77%
Stage #1: With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane
Stage #2: With aluminum (III) chloride In dichloromethane at 20℃;
General procedure: The carboxylic acid (1.1 eq.) was suspended in dry DCM (0.5 m), oxalyl chloride (1 .05 eq.) and a few drops of DMF were added successively. After the gas formation stopped the resulting solution was added dropwise to a suspension of the azaindole (1 eq.) and AICI3(5 eq.) in dry DCM (0.5 m). The mixture was stirred at room temperature for 0.5 - 3h.Saturated, aqueous NH4CI solution was added to quench the reaction. The water phase was extracted with EtOAc (3x), the combined organic layers were dried over Na2S04and the solvent was evaporated under reduced pressure. The product was purified via flash chromatography (Si02, nHex/EtOAc 1 :1 or DCM/MeOH (content of MeOH increased in 0.5percent- steps from 0 to 3percent (v/v)) to yield the titled compound.
Reference: [1] Patent: WO2018/134254, 2018, A1, . Location in patent: Page/Page column 33; 35
[2] Patent: WO2014/159353, 2014, A1, . Location in patent: Paragraph 0055
  • 2
  • [ 1103234-56-5 ]
  • [ 918504-27-5 ]
Reference: [1] Patent: WO2010/129567, 2010, A1,
  • 3
  • [ 1186193-95-2 ]
  • [ 1103234-56-5 ]
YieldReaction ConditionsOperation in experiment
77%
Stage #1: With water; sodium hydroxide In tetrahydrofuran; methanol at 20℃;
Stage #2: With hydrogenchloride In water
Example C2,6-Difluoro-3-(propylsulfonamido)benzoic acidA IN aqueous NaOH solution (150 mL, 150 mmol) was added to a solution of methyl 2,6-difluoro-3-(/V-(propylsulfonyl)propylsulfonamido)benzoate (20.0 g, 50.1 mmol) in 4:1 THF/MeOH (250 mL, 0.2M). The reaction mixture was stirred at room temperature overnight. The majority of the organic solvents were removed in vacuo (water bath temperature 35°C). IN HCl (150 mL) was slowly added to the mixture, and the resulting solid was filtered and rinsed with water (4 X 50 mL). The material was washed with Et2O (4 X 15 mL) to give 2,6-difiuoro- 3-(propylsulfonamido)benzoic acid as a solid (10.7 g, 77percent yield). 1H NMR (400 MHz, d6- DMSO) δ 9.74 (s, IH), 7.57-7.50 (m, IH), 7.23-7.17 (m, IH), 3.11-3.06 (m, 2H), 1.79-1.69 (m, 2H), 0.98 (t, J= 7.4 Hz, 3H). m/z (APCI-neg) M-I = 278.0.
77%
Stage #1: With water; sodium hydroxide In tetrahydrofuran; methanol at 20℃;
Stage #2: With hydrogenchloride In water
A IN aqueous NaOH solution (150 mL, 150 mmol) was added to a solution of methyl 2,6-difluoro-3-(N-(propylsulfonyl)propylsulfonamido)benzoate (20.0 g, 50.1 mmol) in 4:1THF/MeOH (250 mL, 0.2M). The reaction mixture was stirred at room temperature overnight.The majority of the organic solvents were then removed in vacuo (water bath temperature 35°C).IN HCl (150 mL) was slowly added to the mixture, and the resulting solid was filtered and rinsed with water (4 x 50 mL). The material was then washed with Et2O (4 x 15 mL) to give 2,6-difluoro-3-(propylsulfonamido)benzoic acid as a solid (10.7 g, 77percent yield). 1H NMR (400MHz, DMSO- d6) δ 9.74 (s, IH), 7.57-7.50 (m, IH), 7.23-7.17 (m, IH), 3.11-3.06 (m, 2H), 1.79-1.69 (m, 2H), 0.98 (t, J= 7.4 Hz, 3H). m/z (APCI-neg) M-I = 278.0.
77%
Stage #1: With water; sodium hydroxide In tetrahydrofuran; methanol at 20℃;
Stage #2: With hydrogenchloride In water
A IN aqueous NaOH solution (150 mL, 150 mmol) was added to a solution of methyl 2,6-difluoro-3-(N-(propylsulfonyl)propylsulfonamido)benzoate (20.0 g, 50.1 mmol) in 4:1 THF/MeOH (250 mL, 0.2M). The reaction mixture was stirred at room temperature overnight. The majority of the organic solvents were then removed in vacuo (water bath temperature 35°C). IN HCl (150 mL) was slowly added to the mixture, and the resulting solid was filtered and rinsed with water (4 x 50 mL). The material was then washed with Et2O (4 x 15 mL) to give 2,6-difluoro-3-(propylsulfonamido)benzoic acid as a solid (10.7 g, 77percent yield). 1H NMR (400 MHz, DMSO- J6) δ 9.74 (s, IH), 7.57-7.50 (m, IH), 7.23-7.17 (m, IH), 3.11-3.06 (m, 2H), 1.79-1.69 (m, 2H), 0.98 (t, J= 7.4 Hz, 3H). m/z (APCI-neg) M-I = 278.0.
77%
Stage #1: With water; sodium hydroxide In tetrahydrofuran; methanol at 20℃;
Stage #2: With hydrogenchloride; water In tetrahydrofuran; methanol
Example C2,6-Difluoro-3 -(propylsulfonamido)benzoic acid; [00238] A IN aqueous NaOH solution (150 mL, 150 mmol) was added to a solution of methyl 2,6-difluoro-3-(jV-(propylsulfonyl)propylsulfonamido)benzoate (20.0 g, 50.1 mmol) in 4:1 THF/MeOH (250 mL, 0.2M). The reaction mixture was stirred at room temperature overnight. The majority of the organic solvents were removed in vacuo (water bath temperature 35°C). IN HCl (150 mL) was slowly added to the mixture, and the resulting solid was filtered and rinsed with water (4 X 50 mL). The material was washed with Et2O (4 X 15 mL) to give 2,6-difluoro-3-(propylsulfonamido)benzoic acid as a solid (10.7 g, 77percent yield). 1H NMR (400 MHz, (4-DMSO) δ 9.74 (s, IH), 7.57-7.50 (m, IH), 7.23-7.17 (m, IH), 3.11-3.06 (m, 2H), 1.79- 1.69 (m, 2H), 0.98 (t, J= 7.4 Hz, 3H). m/z (APCI-neg) M-I = 278.0.
77%
Stage #1: With water; sodium hydroxide In tetrahydrofuran; methanol at 20℃;
Stage #2: With hydrogenchloride In tetrahydrofuran; methanol; water
Intermediate Example B2,6-difluoro-3 -(propylsulfonamido)benzoic acid[00178] A IN aqueous NaOH solution (150 mL, 150 mmol) was added to a solution of methyl 2,6-difluoro-3-(N-(propylsulfonyl)propylsulfonamido)benzoate (20.0 g, 50.1 mmol) in 4:1 THF/MeOH (250 mL, 0.2M). The reaction mixture was stirred at room temperature overnight. The majority of the organic solvents were then removed in vacuo (water bath temperature 350C). IN HCl (150 niL) was slowly added to the mixture, and the resulting solid was filtered and rinsed with water (4 X 50 mL). The material was then washed with Et2O (4 X 15 mL) to give 2,6-difluoro-3-(propylsulfonamido)benzoic acid as a solid (10.7 g, 77percent yield). 1H NMR (400 MHz, (CDg)2SO) δ 9.74 (s, IH), 7.57-7.50 (m, IH), 7.23-7.17 (m, IH), 3.11-3.06(m, 2H), 1.79-1.69 (m, 2H), 0.98 (t, J = 7.4 Hz, 3H). m/z (APCI-neg) M-I = 278.0.
77% With water; sodium hydroxide In tetrahydrofuran; methanol at 20℃; A IN aqueous NaOH solution (150 mL, 150 mmol) was added to a solution of methyl 2,6-difluoro-3-(N-(propylsulfonyl)propylsulfonamido)benzoate (20.0 g, 50.1 mmol) in 4:1 THF/MeOH (250 mL, 0.2M). The reaction mixture was stirred at room temperature overnight. The majority of the organic solvents were removed in vacuo (water bath temperature 35°C). IN HC1 (150 mL) was slowly added to the mixture, and the resulting solid was filtered and rinsed with water (4 X 50 mL). The material was washed with Et20 (4 X 15 mL) to give 2,6-difluoro-3-(propylsulfonamido)benzoic acid as a solid (10.7 g, 77percent yield). 1H NMR (400 MHz, (CD3)2SO) δ 9.74 (s, 1H), 7.57-7.50 (m, 1H), 7.23-7.17 (m, 1H), 3.11-3.06 (m, 2H), 1.79-1.69 (m, 2H), 0.98 (t, J - 7.4 Hz, 3H). m/z (APCI-neg) M-l = 278.0.
77%
Stage #1: With water; sodium hydroxide In tetrahydrofuran; methanol at 20℃;
Stage #2: With hydrogenchloride In water
A IN aqueous NaOH solution (150 mL, 150 mmol) was added to a solution of methyl 2,6-difluoro-3-(N-(propylsulfonyl)propylsulfonamido)benzoate (20.0 g, 50.1 mmol) in 4:1 THF/MeOH (250 mL, 0.2M). The reaction mixture was stirred at room temperature overnight. The majority of the organic solvents were then removed in vacuo (water bath temperature 35°C). IN HCl (150 mL) was slowly added to the mixture, and the resulting solid was filtered and rinsed with water (4 X 50 mL). The material was then washed with Et2O (4 X 15 mL) to give 2,6-difluoro-3-(propylsulfonamido)benzoic acid as a solid (10.7 g, 77percent yield). 1H NMR (400 MHz, d6-DMSO) δ 9.74 (s, IH), 7.57-7.50 (m, IH), 7.23-7.17 (m, IH), 3.11-3.06 (m, 2H), 1.79-1.69 (m, 2H), 0.98 (t, J = 7.4 Hz, 3H). m/z (APCI-neg) M-I = 278.0.
77%
Stage #1: With water; sodium hydroxide In tetrahydrofuran; methanol at 20℃;
Stage #2: With hydrogenchloride In tetrahydrofuran; methanol; water
2,6-difluoro-3 -(propylsulfonamido)benzoic acid <n="40"/>[00188] A IN aqueous NaOH solution (150 niL, 150 mmol) was added to a solution of methyl 2,6-difluoro-3-(N-(propylsulfonyl)propylsulfonamido)-benzoate (20.0 g, 50.1 mmol) in 4:1 THF/MeOH (250 niL, 0.2M). The reaction mixture was stirred at room temperature overnight. The majority of the organic solvents were then removed in vacuo (water bath temperature 35°C). IN HCl (150 mL) was slowly added to the mixture, and the resulting solid was filtered and rinsed with water (4 X 50 mL). The material was then washed with Et2O (4 X 15 mL) to give 2,6-difluoro-3-(propylsulfonamido)benzoic acid as a solid (10.7 g, 77percent yield). 1H NMR (400 MHz, d6-DMSO) δ 9.74 (s, IH), 7.57-7.50 (m, IH), 7.23-7.17 (m, IH), 3.11-3.06 (m, 2H), 1.79-1.69 (m, 2H), 0.98 (t, J = 7.4 Hz, 3H). m/z (APCI-neg) M-I = 278.0.
77%
Stage #1: With water; sodium hydroxide In tetrahydrofuran; methanol at 20℃;
Stage #2: With hydrogenchloride In water
A IN aqueous NaOH solution (150 mL, 150 mmol) was added to a solution of methyl 2,6-difluoro-3-(N-(propylsulfonyl)propylsulfonamido)benzoate (20.0 g, 50.1 mmol) in 4:1 THF/MeOH (250 mL, 0.2M). The reaction mixture was stirred at room temperature overnight. The majority of the organic solvents were then removed in vacuo (water bath temperature 35°C). IN HCl (150 mL) was slowly added to the mixture, and the resulting solid was filtered and rinsed with water (4 X 50 mL). The material was then washed with Et2O (4 X 15 mL) to give 2,6-difluoro-3-(propylsulfonamido)benzoic acid as a solid (10.7 g, 77percent yield). 1H NMR (400 MHz, d6-DMSO) δ 9.74 (s, IH), 7.57-7.50 (m, IH), 7.23-7.17 (m, IH), 3.11-3.06 (m, 2H), 1.79-1.69 (m, 2H), 0.98 (t, J = 7.4 Hz, 3H). m/z (APCI-neg) M-I == 278.0.
55% With sodium hydroxide In tetrahydrofuran; methanol; water at 0 - 20℃; General procedure: The ester / disulfonamide was dissolved in THF/MeOH (1 m, 4:1 ), cooled to 0°C and treated with NaOHaq(2 M, 2 - 3 eq.). After 10 min. the ice bath was removed and the reaction was stirred at room temperature until complete hydrolysis. THF/MeOH was removed in vacuo, the residual was treated with HCq(2 m) upon precipitating of the product. The precipitate was filtered of, dried and was used without any further purification.

Reference: [1] Patent: WO2011/25938, 2011, A2, . Location in patent: Page/Page column 52
[2] Patent: WO2011/25940, 2011, A1, . Location in patent: Page/Page column 57-58
[3] Patent: WO2011/25947, 2011, A1, . Location in patent: Page/Page column 40
[4] Patent: WO2011/25965, 2011, A1, . Location in patent: Page/Page column 38
[5] Patent: WO2011/25951, 2011, A1, . Location in patent: Page/Page column 31-32
[6] Patent: WO2012/118492, 2012, A1, . Location in patent: Page/Page column 47
[7] Patent: WO2009/111277, 2009, A1, . Location in patent: Page/Page column 39
[8] Patent: WO2009/111280, 2009, A1, . Location in patent: Page/Page column 38-39
[9] Patent: WO2009/111279, 2009, A1, . Location in patent: Page/Page column 66
[10] Patent: WO2018/134254, 2018, A1, . Location in patent: Page/Page column 32; 34; 35
[11] Patent: CN107722013, 2018, A, . Location in patent: Paragraph 0071; 0087; 0088; 0089; 0090
  • 4
  • [ 1186223-50-6 ]
  • [ 1103234-56-5 ]
YieldReaction ConditionsOperation in experiment
96% With water; lithium hydroxide In tetrahydrofuran at 20℃; Step 6: 2,6-difluoro-3-(propylsulfonamido)benzoic acid To a solution of methyl 2,6-difluoro-3-(propylsulfonamido)benzoate (22.3 g, 76 mmol) in THF (100 mL) was added LiOH aqueous (2.5 eq.) and the resulting reaction mixture was stirred at room temperature for overnight. The solvent was removed in vacuo and the residue was neutralized with HCl (6N) to pH1H NMR (DMSC i): ? 9.73 (1H, s), 7.55-7.49 (1H, m), 7.21-7.17 (1H, m), 3.09-3.05 (2H, m), 1.77-1.64 (2H, m), 0.96 (3H, t, J = 7.2 Hz).
96% With lithium hydroxide In tetrahydrofuran; water at 20℃; To a solution of 2,6-difluoro-3-propanesulfonamidobenzoate (22.3 g, 76 mmol) in tetrahydrofenasilane was added an aqueous solution of lithium hydroxide (2.5 equivalents), and the resulting mixture was stirred at room temperature overnight. Vacuum concentration to remove most of the solvent, slowly dropping 6N hydrochloric acid to pH The filter cake was washed with a large amount of water and dried to give the title compound (20.4 g, 96percent).
Reference: [1] Patent: WO2013/71865, 2013, A1, . Location in patent: Page/Page column 26; 27
[2] Patent: CN103102349, 2017, B, . Location in patent: Paragraph 0163-0165
[3] Acta Pharmacologica Sinica, 2017, vol. 38, # 7, p. 1059 - 1068
[4] Patent: WO2018/134254, 2018, A1, . Location in patent: Page/Page column 78
  • 5
  • [ 918523-58-7 ]
  • [ 1103234-56-5 ]
YieldReaction ConditionsOperation in experiment
91% With Oxone In N,N-dimethyl-formamide at 20℃; To a reaction flask, propane-1-sulfonic acid (2,4-difluoro-3-formyl-phenyl)-amide (43, 3.00 g, 11.4 mmol) and oxone (9.10 g, 14.8 mmol) and 30 mL of anhydrous NN-dimethylformamide were added under nitrogen. The mixture was stirred at room temperature overnight, then quenched with 250 mL of 1 M hydrochloric acid solution and extracted with 250 mL of ethyl acetate. The organic layers were washed with 3 x 100 mL of IM hydrochloric acid solution and dried over magnesium sulfate. After removal of drying agent and solvent, the residue was dried in vacuo to provide the desired compound (45, 2.9g, 91percent).
Reference: [1] Patent: WO2009/12283, 2009, A1, . Location in patent: Page/Page column 94
  • 6
  • [ 918523-45-2 ]
  • [ 1103234-56-5 ]
Reference: [1] Patent: WO2010/104945, 2010, A1, . Location in patent: Page/Page column 34
[2] Patent: WO2007/2325, 2007, A1, . Location in patent: Page/Page column 75
[3] Patent: WO2010/129567, 2010, A1, . Location in patent: Page/Page column 80
  • 7
  • [ 83141-10-0 ]
  • [ 1103234-56-5 ]
Reference: [1] Patent: WO2011/25938, 2011, A2,
[2] Patent: WO2011/25940, 2011, A1,
[3] Patent: WO2011/25947, 2011, A1,
[4] Patent: WO2011/25965, 2011, A1,
[5] Patent: WO2011/25951, 2011, A1,
[6] Patent: WO2012/118492, 2012, A1,
[7] Acta Pharmacologica Sinica, 2017, vol. 38, # 7, p. 1059 - 1068
[8] Patent: CN107722013, 2018, A,
[9] Patent: WO2018/134254, 2018, A1,
[10] Patent: WO2018/134254, 2018, A1,
[11] Patent: WO2009/111277, 2009, A1,
[12] Patent: WO2009/111280, 2009, A1,
[13] Patent: WO2009/111279, 2009, A1,
  • 8
  • [ 84832-01-9 ]
  • [ 1103234-56-5 ]
Reference: [1] Patent: WO2011/25938, 2011, A2,
[2] Patent: WO2011/25940, 2011, A1,
[3] Patent: WO2011/25947, 2011, A1,
[4] Patent: WO2011/25965, 2011, A1,
[5] Patent: WO2011/25951, 2011, A1,
[6] Patent: WO2012/118492, 2012, A1,
[7] Patent: WO2013/71865, 2013, A1,
[8] Patent: CN103102349, 2017, B,
[9] Acta Pharmacologica Sinica, 2017, vol. 38, # 7, p. 1059 - 1068
[10] Patent: CN107722013, 2018, A,
[11] Patent: WO2018/134254, 2018, A1,
[12] Patent: WO2018/134254, 2018, A1,
[13] Patent: WO2009/111277, 2009, A1,
[14] Patent: WO2009/111280, 2009, A1,
[15] Patent: WO2009/111279, 2009, A1,
  • 9
  • [ 84832-02-0 ]
  • [ 1103234-56-5 ]
Reference: [1] Patent: WO2011/25940, 2011, A1,
[2] Patent: WO2011/25947, 2011, A1,
[3] Patent: WO2011/25965, 2011, A1,
[4] Patent: WO2011/25938, 2011, A2,
[5] Patent: WO2011/25951, 2011, A1,
[6] Patent: WO2012/118492, 2012, A1,
[7] Patent: WO2013/71865, 2013, A1,
[8] Patent: CN103102349, 2017, B,
[9] Acta Pharmacologica Sinica, 2017, vol. 38, # 7, p. 1059 - 1068
[10] Patent: CN107722013, 2018, A,
[11] Patent: WO2018/134254, 2018, A1,
[12] Patent: WO2018/134254, 2018, A1,
[13] Patent: WO2009/111277, 2009, A1,
[14] Patent: WO2009/111279, 2009, A1,
[15] Patent: WO2009/111280, 2009, A1,
  • 10
  • [ 385-00-2 ]
  • [ 1103234-56-5 ]
Reference: [1] Patent: WO2013/71865, 2013, A1,
[2] Patent: CN103102349, 2017, B,
[3] Acta Pharmacologica Sinica, 2017, vol. 38, # 7, p. 1059 - 1068
[4] Patent: CN107722013, 2018, A,
  • 11
  • [ 918523-44-1 ]
  • [ 1103234-56-5 ]
Reference: [1] Patent: WO2010/129567, 2010, A1,
  • 12
  • [ 367-25-9 ]
  • [ 1103234-56-5 ]
Reference: [1] Patent: WO2010/129567, 2010, A1,
  • 13
  • [ 13671-00-6 ]
  • [ 1103234-56-5 ]
Reference: [1] Patent: WO2013/71865, 2013, A1,
[2] Patent: CN103102349, 2017, B,
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Chemical Structure| 7151-76-0

[ 7151-76-0 ]

4-(Methylsulfonamido)benzoic acid

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Chemical Structure| 83141-11-1

[ 83141-11-1 ]

3-Amino-2,6-difluorobenzoic acid

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Chemical Structure| 914223-43-1

[ 914223-43-1 ]

3-Amino-2-fluorobenzoic acid

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Chemical Structure| 154314-62-2

[ 154314-62-2 ]

4-Amino-2,6-difluorobenzoic acid

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Sulfamides

Chemical Structure| 716361-59-0

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3-Fluoro-4-(methylsulfonamido)benzoic acid

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Chemical Structure| 1195768-19-4

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Methyl 3-(2,6-difluorophenylsulfonamido)-2-fluorobenzoate

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Chemical Structure| 7151-76-0

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4-(Methylsulfonamido)benzoic acid

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Chemical Structure| 107922-46-3

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Methyl 3-benzenesulfonamidobenzoate

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Chemical Structure| 56205-88-0

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4-(Methylsulphonylamino)phenylacetic Acid

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