36016-40-7

Basic information

• Product Name: O-Mesitylenesulfonylhydroxylamine
• Synonyms: O-(MESITYLSULFONYL)HYDROXYLAMINE;O-mesitylenesulphonylhydroxylamine;O-Mesitylenesulfonylhydroxylamine;2-[(Aminooxy)sulfonyl]-1,3,5-trimethylbenzene;O-(2,4,6-Trimethylphenyl)sulfonylhydroxylamine;N-hydroxy-2,4,6-trimethylbenzenesulfonamide ;MSH, O-(Mesitylenesulfonyl)hydroxylamine;O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamine
• CAS NO: 36016-40-7
• Molecular Formula: C₉H₁₃NO₃S
• Molecular Weight: 215.27
• Product Categories: Polyamines
• Mol File: 36016-40-7.mol

Chemical Properties

• Melting Point: 93-94 °C
• Boiling Point: 350.587 °C at 760 mmHg
• Flash Point: 165.83 °C
• Appearance: /
• Density: 1.240
• Vapor Pressure: 1.75E-06mmHg at 25°C
• Refractive Index: 1.556
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly)
• PKA: -4.59±0.70(Predicted)
• Stability: Do not dry. Will explode. Explosive.
• CAS DataBase Reference: O-Mesitylenesulfonylhydroxylamine(CAS DataBase Reference)
• NIST Chemistry Reference: O-Mesitylenesulfonylhydroxylamine(36016-40-7)
• EPA Substance Registry System: O-Mesitylenesulfonylhydroxylamine(36016-40-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 36016-40-7(Hazardous Substances Data)

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

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 
• 51578-88-2 2,3-diamino-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 
• 52197-75-8 3-amino-2-methyl-thiazolium; 2,4,6-trimethyl-benzenesulfonate 
• 51578-94-0 2-acetylamino-3-amino-benzothiazolium; 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 
• 42496-74-2 19α-amino-10-oxo-strychnidinium; 2,4,6-trimethyl-benzenesulfonate 
• 42496-75-3 1α-amino-11-oxo-(2α)-securinanium; 2,4,6-trimethyl-benzenesulfonate 

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Selective inhibition of exclusively transcription-regulating positive transcription elongation factor b/CDK9 is a promising new approach in cancer therapy. Starting from atuveciclib, the first selective CDK9 inhibitor to enter clinical development, lead optimization efforts aimed at identifying intravenously (iv) applicable CDK9 inhibitors with an improved therapeutic index led to the discovery of the highly potent and selective clinical candidate VIP152. The evaluation of various scaffold hops was instrumental in the identification of VIP152, which is characterized by the underexplored benzyl sulfoximine group. VIP152 exhibited the best preclinical overall profile in vitro and in vivo, including high efficacy and good tolerability in xenograft models in mice and rats upon once weekly iv administration. VIP152 has entered clinical trials for the treatment of cancer with promising longterm, durable monotherapy activity in double-hit diffuse large B-cell lymphoma patients.

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.

Pyrimidine-4 (3H)-ketone heterocyclic compound, preparation method thereof and application of pyrimidine-4 (3H)-ketone heterocyclic compound in medicine

The invention relates to pyrimidine-4 (3H)-ketone heterocyclic compounds suitable for inhibiting or regulating SHP2, a preparation method of the pyrimidine-4 (3H)-ketone heterocyclic compounds and application of the pyrimidine-4 (3H)-ketone heterocyclic compounds in medicine. Specifically, the invention relates to a compound as shown in a general formula (I) and a pharmaceutically acceptable salt thereof, a pharmaceutical composition containing the compound or the pharmaceutically acceptable salt thereof, a method for treating and/or preventing related diseases mediated by SHP2, especially cancers by using the compound or the pharmaceutically acceptable salt thereof, and a preparation method of the compound or the pharmaceutically acceptable salt thereof. The invention also relates to application of the compound or the pharmaceutically acceptable salt thereof or a pharmaceutical composition containing the compound or the pharmaceutically acceptable salt thereof in preparation of drugs for treating and/or preventing SHP2-mediated related diseases. Wherein each substituent in the general formula (I) is as defined in the specification.

Divergent and Regioselective Synthesis of Pyrazolo[1,5- a]pyridines and Imidazo[1,5- a]pyridines

Nitrogenous heterocycles are ubiquitous in pharmaceuticals and drug-like compounds; however, regioselective synthesis has proved challenging. Herein we report our efforts to develop a regioselective method for the synthesis of pyrazolo[1,5-a]pyridines and the serendipitous discovery of a protocol for the regioselective formation of imidazo[1,5-a]pyridines. Together, these transformations allow for the rapid and selective formation of two important heterocyclic motifs from a common intermediate.

SUBSTITUTED 1,5-NAPHTHYRIDINES OR QUINOLINES AS ALK5 INHIBITORS

The present disclosure provides inhibitors of activin receptor-like kinase 5 (ALK5). Also disclosed are methods to modulate the activity of ALK5 and methods of treatment of disorders mediated by ALK5.

QUINOXALINE DERIVATIVES

The present invention relates to compounds according to general formula (I), which act as modulators of the glucocorticoid receptor and can be used in the treatment and/or prophylaxis of disorders which are at least partially mediated by the glucocorticoid receptor.