53297-70-4

Usage

Uses

Used in Pharmaceutical Industry:
3-Methyl-4-aminobenzensulfonamide is used as an intermediate in the synthesis of various pharmaceuticals, particularly for the production of sulfonamide-based drugs. Its presence in these drugs contributes to their antibacterial properties, making them effective in treating a range of bacterial infections.
Used in the Treatment of Urinary Tract Infections:
3-Methyl-4-aminobenzensulfonamide is used as an active pharmaceutical ingredient for treating urinary tract infections. Its antibacterial action helps in combating the infection and promoting recovery.
Used in the Treatment of Bacterial Meningitis:
3-Methyl-4-aminobenzensulfonamide is also utilized in the formulation of drugs for the treatment of bacterial meningitis, where its antibacterial properties are crucial in managing the infection and reducing inflammation in the meninges.
Used in Chemical Industry:
3-Methyl-4-aminobenzensulfonamide is used in the manufacturing of dyes, pigments, and herbicides. Its chemical structure allows it to serve as a valuable component in these products, enhancing their performance and effectiveness.

InChI:InChI=1/C7H10N2O2S/c1-5-4-6(12(9,10)11)2-3-7(5)8/h2-4H,8H2,1H3,(H2,9,10,11)

Synthetic route

N-[4-(aminosulfonyl)-2-methylphenyl]acetamide (252562-03-1) → 4-amino-3-methylbenzenesulfonamide (53297-70-4)

Conditions	Yield
With hydrogenchloride In ethanol; water at 80℃;	100%
With hydrogenchloride; water In ethanol Reflux;	100%
Stage #1: N-[4-(aminosulfonyl)-2-methylphenyl]acetamide With hydrogenchloride In ethanol; water Heating / reflux; Stage #2: With sodium hydrogencarbonate In ethanol; water at 20℃;	93%
With hydrogenchloride
With hydrogenchloride In ethanol for 1h; Heating;

4-(acetylamino)-3-methylbenzenesulfonyl chloride (14988-21-7) → 4-amino-3-methylbenzenesulfonamide (53297-70-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: NH4OH / tetrahydrofuran / 0.33 h / 20 °C 2: aq. HCl / ethanol / 1 h / Heating View Scheme
Multi-step reaction with 2 steps 1: ammonium hydroxide / water; tetrahydrofuran / 1 h / 0 - 20 °C 2: hydrogenchloride; water / ethanol / Reflux View Scheme

sodium 4-(acetylamino)-3-methylbenzenesulfonate → 4-amino-3-methylbenzenesulfonamide (53297-70-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: thionyl chloride / dimethylformamide / 2 h / -4 °C 2: NH4OH / tetrahydrofuran / 0.33 h / 20 °C 3: aq. HCl / ethanol / 1 h / Heating View Scheme
Multi-step reaction with 3 steps 1: thionyl chloride / N,N-dimethyl-formamide / 2 h / -40 - 20 °C 2: ammonium hydroxide / water; tetrahydrofuran / 1 h / 0 - 20 °C 3: hydrogenchloride; water / ethanol / Reflux View Scheme

C10H15N3O2S → 4-amino-3-methylbenzenesulfonamide (53297-70-4)

Conditions	Yield
Stage #1: C10H15N3O2S With lithium hydroxide; water In methanol at 50℃; for 5h; Stage #2: With hydrogenchloride In methanol; water at 25℃; for 0.25h; pH=9;

2-aminotoluene-5-sulfonic acid (98-33-9) → 4-amino-3-methylbenzenesulfonamide (53297-70-4)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: pyridine / 2 h / 20 °C 2.1: sodium hydroxide / pyridine / 3 h / 20 °C 2.2: 2 h / -30 - 40 °C 3.1: ammonium hydroxide / tetrahydrofuran / 1 h / 0 - 20 °C 4.1: hydrogenchloride / ethanol; water / 80 °C View Scheme
Multi-step reaction with 5 steps 1: pyridine / 2 h / 20 °C 2: sodium hydroxide / water / 3 h / 20 °C 3: thionyl chloride / N,N-dimethyl-formamide / 2 h / -40 - 20 °C 4: ammonium hydroxide / water; tetrahydrofuran / 1 h / 0 - 20 °C 5: hydrogenchloride; water / ethanol / Reflux View Scheme

4-acetamido-3-methylbenzenesulfonic acid → 4-amino-3-methylbenzenesulfonamide (53297-70-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydroxide / pyridine / 3 h / 20 °C 1.2: 2 h / -30 - 40 °C 2.1: ammonium hydroxide / tetrahydrofuran / 1 h / 0 - 20 °C 3.1: hydrogenchloride / ethanol; water / 80 °C View Scheme
Multi-step reaction with 4 steps 1: sodium hydroxide / water / 3 h / 20 °C 2: thionyl chloride / N,N-dimethyl-formamide / 2 h / -40 - 20 °C 3: ammonium hydroxide / water; tetrahydrofuran / 1 h / 0 - 20 °C 4: hydrogenchloride; water / ethanol / Reflux View Scheme

6-nitro-toluene-3-sulfonic acid amide → 4-amino-3-methylbenzenesulfonamide (53297-70-4)

Conditions	Yield
With palladium on activated charcoal; hydrogen In methanol at 20℃;

[4-chloro-3-(3-chloro-5-cyano-phenoxy)-2-fluoro-phenyl]-acetyl chloride (1007571-96-1) + 4-amino-3-methylbenzenesulfonamide (53297-70-4) → 2-[4-chloro-3-(3-chloro-5-cyano-phenoxy)-2-fluoro-phenyl]-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide

Conditions	Yield
Stage #1: [4-chloro-3-(3-chloro-5-cyano-phenoxy)-2-fluoro-phenyl]-acetyl chloride; 4-amino-3-methylbenzenesulfonamide With sodium hydrogencarbonate In acetone at 20℃; for 24h; Stage #2: With hydrogenchloride In water; acetone at 0℃;	90%

C15H7BrCl2FNO2 (1056598-54-9) + 4-amino-3-methylbenzenesulfonamide (53297-70-4) → 2-[4-Bromo-3-(3-chloro-5-cyano-phenoxy)-2-fluoro-phenyl]-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide

Conditions	Yield
Stage #1: C15H7BrCl2FNO2; 4-amino-3-methylbenzenesulfonamide With sodium hydrogencarbonate In acetone at 0 - 20℃; for 24h; Stage #2: With hydrogenchloride In water; acetone	87%
Stage #1: C15H7BrCl2FNO2; 4-amino-3-methylbenzenesulfonamide With sodium hydrogencarbonate In acetone at 20℃; for 24h; Stage #2: With hydrogenchloride In water; acetone at 0℃;	87%

4-amino-3-methylbenzenesulfonamide (53297-70-4) + 2-Bromoacetyl bromide (598-21-0) → N-[4-(aminosulfonyl)-2-methylphenyl]-2-bromoacetamide (329944-57-2)

Conditions	Yield
With pyridine In chloroform at 20℃;	69%
With pyridine In chloroform at 0 - 20℃; for 18.3333h;	69%

[2-(3-cyanobenzoyl)-4-(trifluoromethyl)phenoxy]acetyl chloride (329943-23-9) + 4-amino-3-methylbenzenesulfonamide (53297-70-4) → 2-[2-(3-cyano-benzoyl)-4-trifluoromethyl-phenoxy]-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide

Conditions	Yield
With sodium hydrogencarbonate In acetone at 20℃; for 2.5h;	53%

3-(2-(3-(5-(2-methyl-1H-imidazol-1-yl)thiophen-2-yl)-3-oxopropyl)-1,3-dioxolan-2-yl)propanoic acid (1338799-46-4) + 4-amino-3-methylbenzenesulfonamide (53297-70-4) → 3-(5-(5-(2-methyl-1H-imidazol-1-yl)thiophen-2-yl)-1-(2-methyl-4-sulfamoylphenyl)-1H-pyrrol-2-yl)propanoic acid (1208317-17-2)

Conditions	Yield
In acetic acid at 120℃;	31%

4-amino-3-methylbenzenesulfonamide (53297-70-4) + 2-((5-bromo-2-chloropyrimidin-4-yl)amino)-6-fluorobenzamide → 2-((5-bromo-2-((2-methyl-4-sulfamoylphenyl)amino)pyrimidin-4-yl)amino)-6-fluorobenzamide

Conditions	Yield
With trifluoroacetic acid In iso-butanol at 100℃; for 16h;	21%

(Z)-9-octadecenoyl chloride (112-77-6) + 4-amino-3-methylbenzenesulfonamide (53297-70-4) → 6-oleoylamino-toluenesulfonamide-(3)

Conditions	Yield
With pyridine

4-amino-3-methylbenzenesulfonamide (53297-70-4) + dibutylamine (111-92-2) + acetyl chloride (75-36-5) → 2-Methyl-benzene-1,4-disulfonic acid 4-(acetyl-amide) 1-dibutylamide

Conditions	Yield
Multistep reaction;

4-amino-3-methylbenzenesulfonamide (53297-70-4) + ({4-chloro-2-[(3-cyanophenyl)carbonyl]phenyl}oxy)acetyl chloride (329944-30-1) → 2-[4-chloro-2-(3-cyano-benzoyl)-phenoxy]-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide

Conditions	Yield
With sodium hydrogencarbonate In acetone at 20℃;	71.25 g

4-amino-3-methylbenzenesulfonamide (53297-70-4) + [4-chloro-2-(3-fluoro-5-trifluoromethylbenzoyl)phenoxy]acetyl chloride (675139-67-0) → GW4511

Conditions	Yield
With sodium hydrogencarbonate In acetone at 20℃; for 24h;	9 g

[(1-mesityl-1H-tetrazol-5-yl)thio]acetic acid (436095-23-7) + 4-amino-3-methylbenzenesulfonamide (53297-70-4) → N-[4-(aminosulfonyl)-2-methylphenyl]-2-[(1-mesityl-1H-tetrazol-5-yl)thio]acetamide

Conditions	Yield
With phosphorus pentachloride In chloroform; toluene at 20 - 70℃;
With phosphorus pentachloride In chloroform; toluene at 20 - 70℃; for 4.5h;

4-amino-3-methylbenzenesulfonamide (53297-70-4) → N-[4-(aminosulfonyl)-2-methylphenyl]-2-iodoacetamide (329944-70-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 69 percent / pyridine / CHCl3 / 20 °C 2: 92 percent / N-[4-(aminosulfonyl)-2-methylphenyl]-2-chloroacetamide; NaI / acetone / 20 h / 20 °C View Scheme

4-amino-3-methylbenzenesulfonamide (53297-70-4) → 2-[2-(3,5-difluoro-benzoyl)-thiophen-3-yloxy]-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide

Conditions	Yield
Multi-step reaction with 2 steps 1: 69 percent / pyridine / CHCl3 / 20 °C 2: 28 percent / K2CO3 / acetone / 6 h / Heating View Scheme

4-amino-3-methylbenzenesulfonamide (53297-70-4) → 2-[4-chloro-2-(3-chloro-5-methyl-benzoyl)-phenoxy]-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide

Conditions	Yield
Multi-step reaction with 3 steps 1: 69 percent / pyridine / CHCl3 / 20 °C 2: 92 percent / N-[4-(aminosulfonyl)-2-methylphenyl]-2-chloroacetamide; NaI / acetone / 20 h / 20 °C 3: 44 percent / K2CO3 / acetone / 22 h View Scheme

4-amino-3-methylbenzenesulfonamide (53297-70-4) → 2-[4-chloro-2-(3,5-dimethyl-benzoyl)-phenoxy]-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide

Conditions	Yield
Multi-step reaction with 3 steps 1: 69 percent / pyridine / CHCl3 / 20 °C 2: 92 percent / N-[4-(aminosulfonyl)-2-methylphenyl]-2-chloroacetamide; NaI / acetone / 20 h / 20 °C 3: 44 percent / K2CO3 / acetone / 22 h View Scheme

4-amino-3-methylbenzenesulfonamide (53297-70-4) → 2-[4-chloro-2-(5-cyano-pyridine-3-carbonyl)-phenoxy]-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide

Conditions	Yield
Multi-step reaction with 2 steps 1: 69 percent / pyridine / CHCl3 / 20 °C 2: 3 percent / K2CO3; NaI / acetone / Heating View Scheme

4-amino-3-methylbenzenesulfonamide (53297-70-4) → 2-[4-chloro-2-(3,5-dimethoxy-benzoyl)-phenoxy]-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide

Conditions	Yield
Multi-step reaction with 2 steps 1: 69 percent / pyridine / CHCl3 / 20 °C 2: 37 percent / K2CO3 / acetone / 22 h View Scheme

4-amino-3-methylbenzenesulfonamide (53297-70-4) → 2-[2-(3-bromo-5-chloro-benzoyl)-4-chloro-phenoxy]-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide

Conditions	Yield
Multi-step reaction with 2 steps 1: 69 percent / pyridine / CHCl3 / 20 °C 2: 17 percent / K2CO3 / acetone / 22 h View Scheme

4-amino-3-methylbenzenesulfonamide (53297-70-4) → 2-[4-chloro-2-(3-cyano-5-methyl-benzoyl)-phenoxy]-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide

Conditions	Yield
Multi-step reaction with 2 steps 1: 69 percent / pyridine / CHCl3 / 20 °C 2: 66 percent / K2CO3 / acetone / 22 h View Scheme

4-amino-3-methylbenzenesulfonamide (53297-70-4) → 2-[2-(3-bromo-5-trifluoromethyl-benzoyl)-4-chloro-phenoxy]-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide

Conditions	Yield
Multi-step reaction with 2 steps 1: 69 percent / pyridine / CHCl3 / 20 °C 2: 3 percent / K2CO3; NaI / acetone / Heating View Scheme

4-amino-3-methylbenzenesulfonamide (53297-70-4) → 2-[4-chloro-2-(3-cyano-5-trifluoromethyl-benzoyl)-phenoxy]-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide

Conditions	Yield
Multi-step reaction with 2 steps 1: 69 percent / pyridine / CHCl3 / 20 °C 2: 38 percent / K2CO3 / acetone / 22 h View Scheme

4-amino-3-methylbenzenesulfonamide (53297-70-4) → N-[4-(aminosulfonyl)-2-methylphenyl]-2-[4-chloro-2-(3-chloro-5-cyanobenzoyl)phenoxy]acetamide

Conditions	Yield
Multi-step reaction with 2 steps 1: 69 percent / pyridine / CHCl3 / 20 °C 2: 12 percent / K2CO3 / acetone / 22 h View Scheme

4-amino-3-methylbenzenesulfonamide (53297-70-4) + chloroacetyl chloride (79-04-9) → N-[4-(aminosulfonyl)-2-methylphenyl]-2-chloroacetamide (53297-88-4)

6-chloropyrimidine-4-carbonyl chloride (263270-52-6) + 4-amino-3-methylbenzenesulfonamide (53297-70-4) → 6-chloro-pyrimidine-4-carboxylic acid (2-methyl-4-sulfamoyl-phenyl)-amide (1114592-11-8)

Conditions	Yield
With triethylamine In dichloromethane at 20℃;
With N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 0℃; for 0.5h;

2-chloro-9-cyclopentyl-7-methyl-7H-purin-8(9H)-one (1124329-94-7) + 4-amino-3-methylbenzenesulfonamide (53297-70-4) → 4-[(9-cyclopentyl-7-methyl-8-oxo-8,9-dihydro-7H-purin-2-yl)-amino]-3-methylbenzenesulfonamide (1124329-10-7)

Conditions	Yield
Stage #1: 2-chloro-9-cyclopentyl-7-methyl-7H-purin-8(9H)-one; 4-amino-3-methylbenzenesulfonamide With toluene-4-sulfonic acid In Methyl isobutyl carbinol at 200℃; for 0.0833333h; Microwave irradiation; Stage #2: With SCX column; ammonia In methanol; Methyl isobutyl carbinol Product distribution / selectivity;
Stage #1: 2-chloro-9-cyclopentyl-7-methyl-7H-purin-8(9H)-one; 4-amino-3-methylbenzenesulfonamide With toluene-4-sulfonic acid In butan-1-ol at 200℃; for 0.0833333h; Microwave irradiation; Stage #2: With SCX column; ammonia In methanol; butan-1-ol Product distribution / selectivity;

7-methoxy-2-oxo-8-propyl-2H-chromene-3-carboxylic acid (952504-50-6) + 4-amino-3-methylbenzenesulfonamide (53297-70-4) → N-[4-(aminosulfonyl)-2-methylphenyl]-7-methoxy-2-oxo-8-propyl-2H-chromene-3-carboxamide (1296198-11-2)

Conditions	Yield
Stage #1: 7-methoxy-2-oxo-8-propyl-2H-chromene-3-carboxylic acid With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In dichloromethane; ethyl acetate at 20℃; for 0.5h; Stage #2: 4-amino-3-methylbenzenesulfonamide In dichloromethane; ethyl acetate at 20℃;

Upstream product

• 252562-03-1 N-[4-(aminosulfonyl)-2-methylphenyl]acetamide 
• 98-33-9 2-aminotoluene-5-sulfonic acid 
• 14988-21-7 4-(acetylamino)-3-methylbenzenesulfonyl chloride 

Downstream Products

• 1124329-10-7 4-[(9-cyclopentyl-7-methyl-8-oxo-8,9-dihydro-7H-purin-2-yl)-amino]-3-methylbenzenesulfonamide 
• 1234481-10-7 XMD-12-3-1 
• 1341199-23-2 N-[4-(aminosulfonyl)-2-methylphenyl]-2-(4-chloro-2-nitrophenoxy)acetamide 
• 1416364-06-1 C₂₆H₂₂ClN₃O₅S 
• 1416364-05-0 C₂₆H₂₂ClN₃O₅S 
• 1416364-04-9 C₂₃H₂₀Cl₃N₃O₅S 

Relevant academic research and scientific papers

Discovery of a Series of 5,11-Dihydro-6H-benzo[e]pyrimido[5,4-b][1,4]diazepin-6-ones as Selective PI3K-δ/γ Inhibitors

Dual inhibition of PI3K-δ and PI3K-γ is an established therapeutic strategy for treatment of hematological malignancies. Reported molecules targeting PI3K-δ/γ selectively are chemically similar and based upon isoquinolin-1(2H)-one or quinazolin-4(3H)-one scaffolds. Here we report a chemically distinct series of potent, selective PI3K-δ/γ inhibitors based on a 5,11-dihydro-6H-benzo[e]pyrimido[5,4-b][1,4]diazepin-6-one scaffold with comparable biochemical potency and cellular effects on PI3K signaling. We envisage these molecules will provide useful leads for development of next-generation PI3K-δ/γ targeting therapeutics.

Pyrrole inhibitors of S-nitrosoglutathione reductase as therapeutic agents

The present invention is directed to inhibitors of S-nitrosoglutathione reductase (GSNOR), pharmaceutical compositions comprising such GSNOR inhibitors, and methods of making and using the same.

Structure-activity relationship of pyrrole based S-nitrosoglutathione reductase inhibitors: Carboxamide modification

The enzyme S-nitrosoglutathione reductase (GSNOR) is a member of the alcohol dehydrogenase family (ADH) that regulates the levels of S-nitrosothiols (SNOs) through catabolism of S-nitrosoglutathione (GSNO). GSNO and SNOs are implicated in the pathogenesis of many diseases including those in respiratory, gastrointestinal, and cardiovascular systems. The pyrrole based N6022 was recently identified as a potent, selective, reversible, and efficacious GSNOR inhibitor which is currently in clinical development for acute asthma. We describe here the synthesis and structure-activity relationships (SAR) of novel pyrrole based analogs of N6022 focusing on carboxamide modifications on the pendant N-phenyl moiety. We have identified potent and novel GSNOR inhibitors that demonstrate efficacy in an ovalbumin (OVA) induced asthma model in mice.

Process for preparing reverse transcriptase inhibitors

The present invention is directed to processes for the synthesis of intermediates useful in the preparation of non-nucleoside reverse transcriptase inhibitors.

BENZOPHENONES AS INHIBITORS OF REVERSE TRANSCRIPTASE

The present invention includes benzophenone compounds (I) which are useful in the treatment of HIV infections.

Novel Benzophenones as Non-nucleoside Reverse Transcriptase Inhibitors of HIV-1

GW4511, GW4751, and GW3011 showed IC50 values ≤2 nM against wild type HIV-1 and 10 nM against 16 mutants. They were particularly potent against NNRTI-resistant viruses containing Y181C-, K103N-, and K103N-based double mutations, which account for a significant proportion of the clinical failure of the three currently marketed NNRTIs. The antiviral data together with the favorable pharmacokinetic data of GW4511 suggested that these benzophenones possess attributes of a new NNRTI drug candidate.