36016-40-7

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 38, p. 1239, 1973 DOI: 10.1021/jo00946a045Synthesis, p. 788, 1975 DOI: 10.1055/s-1975-23927

InChI:InChI=1/C9H13NO3S/c1-6-4-7(2)9(8(3)5-6)14(12,13)10-11/h4-5,10-11H,1-3H3

Synthetic route

N-(tert-butoxycarbonyl)-O-(mesitylsulfonyl)hydroxylamine (36016-39-4) → mesitylenesulfonylhydroxylamine (36016-40-7)

Conditions	Yield
With trifluoroacetic acid at 0℃; for 1.5h;	100%
With trifluoroacetic acid In 1,4-dioxane at 0 - 20℃; for 2.75h; Industrial scale;	100%
With trifluoroacetic acid at 0℃; for 2h;	100%

ethyl O-(2-mesitylenesulfonyl)acetohydroxamate (38202-27-6) → mesitylenesulfonylhydroxylamine (36016-40-7)

Conditions	Yield
With perchloric acid In 1,4-dioxane; water at 0℃; for 0.116667h;	93%
Stage #1: ethyl O-(2-mesitylenesulfonyl)acetohydroxamate With perchloric acid In 1,4-dioxane; water at 0℃; for 0.116667h; Stage #2: With potassium carbonate In diethyl ether	93%
With perchloric acid In 1,4-dioxane at 0℃; for 0.116667h;	93%

2-mesitylenesulphonyl chloride (773-64-8) → mesitylenesulfonylhydroxylamine (36016-40-7)

Conditions	Yield
Stage #1: 2-mesitylenesulphonyl chloride With triethylamine at 20℃; Stage #2: With perchloric acid Neat (no solvent);	84%
Multi-step reaction with 2 steps 1: 70.1 percent / Et3N / dimethylformamide / 0.5 h / 20 °C 2: aq. HClO4 / dioxane / 0.33 h / -5 °C View Scheme
Multi-step reaction with 2 steps 1: Et3N / dimethylformamide 2: aq. HClO4 / dioxane View Scheme

(Z)-ethyl N-(mesitylsulfonyl)oxyacetimidate → mesitylenesulfonylhydroxylamine (36016-40-7)

Conditions	Yield
With perchloric acid In tetrahydrofuran; water at 0 - 5℃; for 1.33333h; Inert atmosphere;	81.3%
With perchloric acid In 1,4-dioxane for 0.383333h; Cooling; Inert atmosphere;
With perchloric acid; water In tetrahydrofuran at 0 - 5℃; for 1.5h; Inert atmosphere;

ethyl (1E)-N-(2,4,6-trimethylphenyl)sulfonyloxyethanimidate (1239506-69-4) → mesitylenesulfonylhydroxylamine (36016-40-7)

Conditions	Yield
With perchloric acid In 1,4-dioxane at 0℃; for 1.5h; Inert atmosphere;	73%
With perchloric acid In 1,4-dioxane at 0℃; for 1.5h;	73%
With perchloric acid In 1,4-dioxane ice-cooling;

5-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentanal + sodium 1,1,1,3,3,3-hexafluoro-2-propyloxide + O-(1,1,1, 3,3,3-hexafluoro-2-propyl)hydroxylamine → mesitylenesulfonylhydroxylamine (36016-40-7)

Conditions	Yield
With hydrogenchloride In diethyl ether	50%

O-(2,4,6-trimethylphenylsulfonyl)-N,N-bis(trimethylsilyl)hydroxylamine (58658-55-2) → mesitylenesulfonylhydroxylamine (36016-40-7)

Conditions	Yield
With hydrogenchloride In methanol

ethyl O-(2-mesitylenesulphonyl)acetohydroxamate → mesitylenesulfonylhydroxylamine (36016-40-7)

Conditions	Yield
With perchloric acid In 1,4-dioxane
With perchloric acid In 1,4-dioxane; water at 0℃; for 0.25h;	5.26 g

mesitiylenesulfonyl acetoxyhydroxamate → mesitylenesulfonylhydroxylamine (36016-40-7)

Conditions	Yield
With perchloric acid In 1,4-dioxane at 0 - 5℃; for 0.166667h;
With perchloric acid

2-chloro-dibenzo[b,f]thiepine-5-oxide (58288-83-8) → 2-chloro-5,5-dihydro-5-imino-dibenzo[b,f]thiepine-5-oxide (58288-73-6) + mesitylenesulfonylhydroxylamine (36016-40-7)

n-butyllithium (109-72-8, 29786-93-4) + tricarbonyl(tetrachlorobromocyclopentadienyl)manganese + O-(2,4,6-trimethylphenylsulfonyl)-N,N-bis(trimethylsilyl)hydroxylamine (58658-55-2) → tricarbonyl(tetrachloro(H)cyclopentadienyl)manganese + tricarbonyl(tetrachloro(N(SiMe3)2)cyclopentadienyl)manganese + mesitylenesulfonylhydroxylamine (36016-40-7)

Conditions

Yield

In diethyl ether To (C5Cl4Br)Mn(CO)3 in Et2O is added first BuLi at -60°C and then is added MesSO2ON(SiMe3)2 under N2, reaction mixture is warmed up to room temp.; evapn. of Et2O under vac., residue is stirred with hexane, hexane soluble part is washed (H2O), dried over MgSO4, and filtered, addn. of Et2O, H2O and HCl, sepn. of the orange ether phase and drying, filtn., after addn. of hexane ppt. is obtained;

A n/a B 0% C n/a

ethyl O-(mesitylenesulfonyl)acetohydroxamate → mesitylenesulfonylhydroxylamine (36016-40-7)

Conditions	Yield
With perchloric acid In 1,4-dioxane at 0℃; for 0.166667h;

2-Mesitylenesulfonyl chloride → mesitylenesulfonylhydroxylamine (36016-40-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / N,N-dimethyl-formamide / 0.75 h / 0 °C 2: perchloric acid / 1,4-dioxane / 0.75 h / 0 °C View Scheme
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 0.75 h / 0 °C 2: perchloric acid / 1,4-dioxane / 0.75 h / 0 °C View Scheme

(Z)-(ethyl N-[[(2,4,6-trimethylbenzene)sulfonyl] oxy]ethenecarboximidate) → mesitylenesulfonylhydroxylamine (36016-40-7)

Conditions	Yield
With perchloric acid In 1,4-dioxane at 0℃; for 1h;

ethyl O-(mesitylenesulfonyl)acetohydroxamate → mesitylenesulfonylhydroxylamine (36016-40-7)

Conditions	Yield
With perchloric acid In 1,4-dioxane; water Inert atmosphere;

3-Bromopyridine (626-55-1) + mesitylenesulfonylhydroxylamine (36016-40-7) → 1-amino-3-bromopyridin-1-ium 2,4,6-trimethylbenzenesulfonate (55899-13-3)

Conditions	Yield
Stage #1: 3-Bromopyridine; mesitylenesulfonylhydroxylamine In acetonitrile at 30℃; for 0.0166667h; Flow reactor; Stage #2: With sodium hydroxide In N,N-dimethyl-formamide at 30℃; for 0.0433333h; Flow reactor;	100%
In dichloromethane for 0.5h; Ambient temperature;	88%
In dichloromethane 1.) -5 deg C to RT, 2.) RT, 15 min;	68%
In dichloromethane at 0℃; for 1h;

methyl-2,3-diaza-4-methyl-4-acetoxypent-2-enoate (21732-11-6) + mesitylenesulfonylhydroxylamine (36016-40-7) → C9H12O3S*C5H11N3O2 (81549-06-6)

Conditions	Yield
In diethyl ether for 1h; Ambient temperature;	100%

mesitylenesulfonylhydroxylamine (36016-40-7) + 3-acetyl-8-ethyl-2-methylsulfanyl-1H-quinolin-4-one → 2,4,6-trimethylbenzenesulfonic acid methyl ester (70920-59-1) + 8-ethyl-3-methyl-9H-isothiazolo[5,4-b]quinolin-4-one

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 0.0833333h;	A 8% B 100%

mesitylenesulfonylhydroxylamine (36016-40-7) + 3-acetyl-2-benzylsulfanyl-1H-quinolin-4-one → 2,4,6-trimethylbenzenesulfonic acid methyl ester (70920-59-1) + 3-methyl-9H-isothiazolo[5,4-b]quinolin-4-one

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 0.0833333h;	A 8% B 100%

mesitylenesulfonylhydroxylamine (36016-40-7) + C22H20S → C9H11O3S(1-)*C22H22NS(1+)

Conditions	Yield
In dichloromethane at -35℃; for 36h;	100%

4-trifluoromethylpyridine (3796-24-5) + mesitylenesulfonylhydroxylamine (36016-40-7) → 1-amino-4-trifluoromethylpyridinium 2,4,6-trimethylbenzenesulfonate (1299420-32-8)

Conditions	Yield
In dichloromethane at 0 - 20℃; for 18h;	100%
In dichloromethane at 0 - 20℃; for 21h;

tert-butyl 1-(4-(3-phenylpyridin-2-yl)phenyl)cyclobutylcarbamate (1357159-18-2) + mesitylenesulfonylhydroxylamine (36016-40-7) → 1-amino-2-(4-(1-(tert-butoxycarbonylamino)cyclobutyl)phenyl)-3-phenylpyridinium 2,4,6-trimethylbenzenesulfonate (1357159-20-6)

Conditions	Yield
In dichloromethane at 0 - 20℃; for 7h; Inert atmosphere;	100%

methyl 2-(5-bromopyridin-2-yl)acetate (917023-06-4) + mesitylenesulfonylhydroxylamine (36016-40-7) → C9H11O3S(1-)*C8H10BrN2O2(1+)

Conditions	Yield
Stage #1: methyl 2-(5-bromopyridin-2-yl)acetate; mesitylenesulfonylhydroxylamine In acetonitrile at 30℃; Flow reactor; Stage #2: With sodium hydroxide In N,N-dimethyl-formamide at 30℃; Flow reactor;	100%

methyl 2-pyridylacetate (1658-42-0) + mesitylenesulfonylhydroxylamine (36016-40-7) → C9H11O3S(1-)*C8H11N2O2(1+)

Conditions	Yield
Stage #1: methyl 2-pyridylacetate; mesitylenesulfonylhydroxylamine In acetonitrile at 30℃; Flow reactor; Stage #2: With sodium hydroxide In N,N-dimethyl-formamide at 30℃; Flow reactor;	100%

4-pyridinecarboxylic acid, methyl ester (2459-09-8) + mesitylenesulfonylhydroxylamine (36016-40-7) → 1-amino-4-(methoxycarbonyl)pyridin-1-ium 2,4,6-trimethylbenzene-1-sulfonate (59247-63-1)

Conditions	Yield
Stage #1: 4-pyridinecarboxylic acid, methyl ester; mesitylenesulfonylhydroxylamine In acetonitrile at 30℃; for 0.0166667h; Flow reactor; Stage #2: With sodium hydroxide In N,N-dimethyl-formamide at 30℃; for 0.0433333h; Flow reactor;	100%
In dichloromethane at 0 - 20℃; for 21h; Inert atmosphere;	72%

3-(tert-butoxycarbonylamino)pyridine (56700-70-0) + mesitylenesulfonylhydroxylamine (36016-40-7) → 1-amino-3-[(tert-butoxycarbonyl)amino]pyridinium 2,4,6-trimethylbenzenesulfonate

Conditions	Yield
Stage #1: 3-(tert-butoxycarbonylamino)pyridine; mesitylenesulfonylhydroxylamine In acetonitrile at 30℃; for 0.0166667h; Flow reactor; Stage #2: With sodium hydroxide In N,N-dimethyl-formamide at 30℃; for 0.0433333h; Flow reactor;	100%

picoline (108-89-4) + mesitylenesulfonylhydroxylamine (36016-40-7) → 1-amino-4-methylpyridin-1-ium 2,4,6-trimethylbenzene sulfonate (51135-56-9)

Conditions	Yield
In dichloromethane at 0 - 20℃; for 2h;	99%
In dichloromethane at 0 - 20℃; for 2h;	99%
In dichloromethane at 25℃; for 1h;

mesitylenesulfonylhydroxylamine (36016-40-7) + 2-methylsulfanyl-3-acetyl-1H-quinolin-4-one (548929-67-5) → 2,4,6-trimethylbenzenesulfonic acid methyl ester (70920-59-1) + 3-methyl-9H-isothiazolo[5,4-b]quinolin-4-one

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 0.0833333h;	A 8% B 99%

mesitylenesulfonylhydroxylamine (36016-40-7) + 3-acetyl-2-methylsulfanyl-8-phenyl-1H-quinolin-4-one → 2,4,6-trimethylbenzenesulfonic acid methyl ester (70920-59-1) + 3-methyl-8-phenyl-9H-isothiazolo[5,4-b]quinolin-4-one

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 0.0833333h;	A 8% B 99%

2,3-dimethylquinoline (1721-89-7) + mesitylenesulfonylhydroxylamine (36016-40-7) → 2,4,6-Trimethyl-benzenesulfonate1-amino-2,3-dimethyl-quinolinium; (84689-30-5)

Conditions	Yield
In dichloromethane for 1h; Ambient temperature;	98%

2,5-dimethylpyridine (589-93-5) + mesitylenesulfonylhydroxylamine (36016-40-7) → 2,4,6-Trimethyl-benzenesulfonate1-amino-2,5-dimethyl-pyridinium; (81450-83-1)

Conditions	Yield
In dichloromethane for 0.5h; cooling;	98%

2,8-dimethylquinoline (1463-17-8) + mesitylenesulfonylhydroxylamine (36016-40-7) → 2,8-dimethyl-1-aminoquinolinium mesitylenesulphonate (84689-28-1)

Conditions	Yield
In dichloromethane for 1h; Ambient temperature;	98%
In dichloromethane at 25℃; for 0.25h;

mesitylenesulfonylhydroxylamine (36016-40-7) + 5-methoxy-1-methyl-isoquinoline (84689-37-2) → 2,4,6-Trimethyl-benzenesulfonate2-amino-5-methoxy-1-methyl-isoquinolinium; (84689-40-7)

Conditions	Yield
In dichloromethane for 1h; Ambient temperature;	98%

mesitylenesulfonylhydroxylamine (36016-40-7) + 1-{2-[3-(6-methylquinolin-2-yl)propyl]phenyl}-2-phenylethane-1,2-dione (229177-89-3) → 1-amino-6-methyl-2-{3-[2-(2-oxo-2-phenylacetyl)phenyl]propyl}quinolinium mesitylenesulfonate

Conditions	Yield
In dichloromethane at 20℃; for 1h;	98%
In dichloromethane at 20℃; amination;	95%

mesitylenesulfonylhydroxylamine (36016-40-7) + 3-acetyl-6-chloro-2-methylsulfanyl-1H-quinolin-4-one (548929-92-6) → 2,4,6-trimethylbenzenesulfonic acid methyl ester (70920-59-1) + 6-chloro-3-methyl-9H-isothiazolo[5,4-b]quinolin-4-one

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 0.0833333h;	A 8% B 98%

mesitylenesulfonylhydroxylamine (36016-40-7) + 3-acetyl-6-methoxy-2-(methylthio)quinolin-4(1H)-one → 2,4,6-trimethylbenzenesulfonic acid methyl ester (70920-59-1) + 6-methoxy-3-methyl-9H-isothiazolo[5,4-b]quinolin-4-one

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 0.0833333h;	A 8% B 98%

mesitylenesulfonylhydroxylamine (36016-40-7) + 3-acetyl-6-chloro-2-methylsulfanyl-8-trifluoromethyl-1H-quinolin-4-one (548929-96-0) → 2,4,6-trimethylbenzenesulfonic acid methyl ester (70920-59-1) + 6-chloro-3-methyl-8-trifluoromethyl-9H-isothiazolo[5,4-b]quinolin-4-one

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 0.0833333h;	A 8% B 98%

2,5-dimethyl-pyrazine (123-32-0) + mesitylenesulfonylhydroxylamine (36016-40-7) → 1-Amino-2,5-dimethylpyrazin-1-ium-2,4,6-trimethylbenzenesulfonate

Conditions	Yield
In dichloromethane at 0℃; for 1h;	97%
In dichloromethane for 0.333333h; Ambient temperature;	89%

3-methylisoquinoline (1125-80-0) + mesitylenesulfonylhydroxylamine (36016-40-7) → 2,4,6-Trimethyl-benzenesulfonate2-amino-3-methyl-isoquinolinium; (84900-31-2)

Conditions	Yield
In dichloromethane for 1h;	97%

5-bromo-2-pyridylamine (1072-97-5) + mesitylenesulfonylhydroxylamine (36016-40-7) → (1,2-diamino-5-bromopyridin-1-ium) 2,4,6-trimethylbenzenesulfonate (1202704-57-1)

Conditions	Yield
at 0 - 20℃; for 20h; Inert atmosphere;	97%
In chloroform at 20℃; for 3h;	87%
In dichloromethane at 20℃; Cooling with ice;
In chloroform at 0 - 20℃; for 3h;

mesitylenesulfonylhydroxylamine (36016-40-7) + C22H20S → C9H11O4S(1-)*C22H22NS(1+)

Conditions	Yield
In dichloromethane at -35℃; for 24h;	97%

3-bromo-5-methoxypyridine (50720-12-2) + mesitylenesulfonylhydroxylamine (36016-40-7) → 1-amino-3-bromo-5-methoxypyridin-1-ium 2,4,6-trimethylbenzene-1-sulfonate

Conditions	Yield
In 1,2-dichloro-ethane at 5 - 20℃; for 12h; Industrial scale;	97%
In dichloromethane at 0℃; for 3h;	83%
In dichloromethane at 0℃; for 3h;	83%

N-(pyridin-3-yl)acetamide (5867-45-8) + mesitylenesulfonylhydroxylamine (36016-40-7) → 2,4,6-Trimethyl-benzenesulfonate3-acetylamino-1-amino-pyridinium; (55899-08-6)

Conditions	Yield
In dichloromethane for 0.5h; Ambient temperature;	96%

2,6-dimethylquinoline (877-43-0) + mesitylenesulfonylhydroxylamine (36016-40-7) → 2,4,6-Trimethyl-benzenesulfonate1-amino-2,6-dimethyl-quinolinium; (84689-26-9)

Conditions	Yield
In dichloromethane for 1h; Ambient temperature;	96%

Upstream product

• 58658-55-2 O-(2,4,6-trimethylphenylsulfonyl)-N,N-bis(trimethylsilyl)hydroxylamine 
• 773-64-8 2-mesitylenesulphonyl chloride 
• 109-72-8 n-butyllithium 
• 108-67-8 1,3,5-trimethyl-benzene 
• 1239506-69-4 ethyl (1E)-N-(2,4,6-trimethylphenyl)sulfonyloxyethanimidate 
• 58288-83-8 2-chloro-dibenzo[b,f]thiepine-5-oxide 
• 36016-39-4 N-(tert-butoxycarbonyl)-O-(mesitylsulfonyl)hydroxylamine 
• 38202-27-6 ethyl O-(2-mesitylenesulfonyl)acetohydroxamate 

Downstream Products

• 51578-86-0 2,3-diamino-thiazolium; 2,4,6-trimethyl-benzenesulfonate 
• 53995-67-8 2,3-diamino-4-methyl-thiazolium; 2,4,6-trimethyl-benzenesulfonate 
• 53995-64-5 3-amino-2-formylamino-thiazolium; 2,4,6-trimethyl-benzenesulfonate 
• 52197-79-2 3-amino-2-methyl-benzothiazolium; 2,4,6-trimethyl-benzenesulfonate 
• 51578-90-6 2-acetylamino-3-amino-thiazolium; 2,4,6-trimethyl-benzenesulfonate 
• 55738-17-5 1-amino-3-(2-methyl-[1,3]dioxolan-2-yl)-pyridinium; 2,4,6-trimethyl-benzenesulfonate 
• 51578-92-8 3-amino-2-benzoylamino-thiazolium; 2,4,6-trimethyl-benzenesulfonate 
• 51578-98-4 3-amino-2-benzoylamino-4-methyl-thiazolium; 2,4,6-trimethyl-benzenesulfonate 
• 51578-96-2 3-amino-2-benzoylamino-benzothiazolium; 2,4,6-trimethyl-benzenesulfonate 
• 56000-36-3 1,4-diaminopyridinium mesitylenesulphonate 
• 39996-52-6 1-Amino-2-chlorpyridinium-(mesitylen-2-sulfonat) 
• 81450-88-6 2,4,6-Trimethyl-benzenesulfonate1-amino-3,4-dimethyl-pyridinium; 
• 139242-96-9 2,4,6-Trimethyl-benzenesulfonate1-amino-3,6-dimethyl-pyridazin-1-ium; 
• 53975-28-3 N-amino-4,6-dimethylpyrimidinium mesitylene sulfonate 

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N-(4-FLUOROPHENYL)-5-PHENYL-[1,2,4] TRIAZOLO [1,5-A] PYRIDINE-2-CARBOXAMIDE DERIVATIVES AND THEIR SYNTHESIS THEREOF

The present invention relates to the development of novel N-(4-fluorophenyl)-5-phenyl- [1,2,4]triazolo[1,5-a]pyridine-2-carboxamide derivatives for their different pharmacological activities. It particularly relates to the development of N-(4-fluorophenyl)-5-phenyl- [1,2,4]triazolo[1,5-a]pyridine-2-carboxamide derivatives as antiviral, anticancer, antifungal, hypoglycemic, anti-tubercular, sedative, anti-type 2 diabetes activity. It specifically relates to the N-(4-fluorophenyl)-5-phenyl-[1,2,4]triazolo[1,5-a]pyridine-2-carboxamide derivatives for treatment of H37Rv and multidrug-resistant (MDR) strains of Mycobacterium tuberculosis (MTB). The present invention also relates to the process for synthesis of N-(4-fluorophenyl)- 5-phenyl-[1,2,4]triazolo[1,5-a]pyridine-2-carboxamide derivatives. The invention further relates to method for treatment of method for treatment of diseases such as tuberculosis, type 2 diabetes, bacterial, viral and fungal infections. Invention addresses the challenges in working with chemical processes and products by inventing novel reaction methodology that can maximize the desired products and minimize by-products, designing new synthetic schemes that can simplify operations in chemical productions and seeking nontoxic reagent that are inherently environmentally and ecologically benign. Synthesis of novel N-(4- fluorophenyl)-5-phenyl-[1,2,4]triazolo[1,5-a]pyridine-2-carboxamide derivatives is being employed to develop a novel synthetic methodology and their pharmacological applications. Novel series of N-(4-fluorophenyl)-5-phenyl-[1,2,4]triazolo[l,5-a]pyridine-2-carboxamide derivatives were designed synthesized evaluated for their in vitro anti-mycobacterial activity against H37Rv and multi-drug-resistant (MDR) strains of mycobacterium tuberculosis (MTB). All the synthesized compounds were characterized by spectroscopic methods like Mass, NMR and elemental analysis.

AROMATIC RING DERIVATIVE AS IMMUNOREGULATION AND PREPARATION METHOD AND APPLICATION OF AROMATIC RING DERIVATIVE

Relating to a compound represented by formula (I) and a pharmaceutically acceptable salt of the compound, and an application of the compound as an S1P1 agonist.

PYRIMIDINYL GROUP-CONTAINING TRICYCLIC COMPOUND SERVING AS C-MET INHIBITOR

Disclosed are a pyrimidinyl group-containing tricyclic compound and applications thereof in preparing a cancer-treating medicament. Specifically disclosed are a compound as represented by formula (I), a pharmaceutically acceptable salt of same, or an isomer thereof.