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3-[3-Fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)-3-pyridinyl]phenyl]-5-(hydroxymethyl)-2-oxazolidinone
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Name

3-[3-Fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)-3-pyridinyl]phenyl]-5-(hydroxymethyl)-2-oxazolidinone

 EINECS 815-370-6
CAS No. 856866-72-3 Density 1.57
PSA 106.26000 LogP 1.46070
Solubility N/A Melting Point 201 °C
Formula C17H15FN6O3 Boiling Point 614.5±65.0 °C(Predicted)
Molecular Weight 370.343 Flash Point N/A
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 856866-72-3 (Torezolid) Hazard Symbols N/A
Synonyms

Torezolid

Article Data 19

3-[3-Fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)-3-pyridinyl]phenyl]-5-(hydroxymethyl)-2-oxazolidinone Synthetic route

C23H29FN6O3Si

856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

Conditions
ConditionsYield
With cesium fluoride In tetrahydrofuran at 20℃; for 1h;99%
1220910-89-3

3-fluoro-4-(6-(2-methyl-2H-tetrazole-5-yl)pyridin-3-yl)phenyl-carbamic acid benzylester

856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

Conditions
ConditionsYield
With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; tert.-butyl lithium; (R)-glycidyl butyrate In tetrahydrofuran at 0 - 30℃; for 15h; Reagent/catalyst; Large scale;95%
1220910-89-3

3-fluoro-4-(6-(2-methyl-2H-tetrazole-5-yl)pyridin-3-yl)phenyl-carbamic acid benzylester

60456-26-0

(R)-glycidyl butyrate

856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

Conditions
ConditionsYield
Stage #1: 3-fluoro-4-(6-(2-methyl-2H-tetrazole-5-yl)pyridin-3-yl)phenyl-carbamic acid benzylester With potassium tert-butylate; lithium tert-butoxide In tetrahydrofuran; acetonitrile at 25℃; for 2h; Inert atmosphere;
Stage #2: (R)-glycidyl butyrate In tetrahydrofuran; acetonitrile for 3h;		86.7%
Stage #1: 3-fluoro-4-(6-(2-methyl-2H-tetrazole-5-yl)pyridin-3-yl)phenyl-carbamic acid benzylester With lithium hexamethyldisilazane In tetrahydrofuran at 20℃; for 1.41667h; Inert atmosphere;
Stage #2: (R)-glycidyl butyrate With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone In tetrahydrofuran at 20℃; for 15h; Inert atmosphere; cooling with ice;		85%
Stage #1: 3-fluoro-4-(6-(2-methyl-2H-tetrazole-5-yl)pyridin-3-yl)phenyl-carbamic acid benzylester With lithium hexamethyldisilazane In tetrahydrofuran at 10 - 15℃; for 2h; Inert atmosphere; Large scale;
Stage #2: (R)-glycidyl butyrate With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone In tetrahydrofuran at 0 - 15℃; Inert atmosphere; Large scale;		84.4%
1056039-83-8

2-(2-methyl-2H-tetrazol-5-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

444335-16-4

(5R)-3-(4-bromo-3-fluorophenyl)-5-(hydroxymethyl)oxazolidin-2-one

856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate; triphenylphosphine In 1,4-dioxane at 20℃; Reagent/catalyst; Solvent; Temperature; Reflux; Inert atmosphere;84%
With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; tricyclohexylphosphine In 1,4-dioxane; water for 4h; Reagent/catalyst; Solvent; Suzuki Coupling; Inert atmosphere; Reflux;78%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene for 12h; Solvent; Reflux; Inert atmosphere;63.7%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate Suzuki Coupling;
Stage #1: 2-(2-methyl-2H-tetrazol-5-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine; (R)-3-(4-bromo-3-fluorophenyl)-5-(hydroxylmethyl)oxazolidin-2-one With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane at 60℃; for 5h; Suzuki Coupling; Inert atmosphere; Large scale;
Stage #2: With L-Cysteine; triethylamine at 60℃; for 16h; Inert atmosphere; Darkness; Large scale;
444335-16-4

(5R)-3-(4-bromo-3-fluorophenyl)-5-(hydroxymethyl)oxazolidin-2-one

380380-64-3

5-bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine

856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

Conditions
ConditionsYield
Stage #1: (R)-3-(4-bromo-3-fluorophenyl)-5-(hydroxylmethyl)oxazolidin-2-one With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; bis(pinacol)diborane In dimethyl sulfoxide at 80℃; for 14h; Inert atmosphere;
Stage #2: 5-bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate In 1,4-dioxane; water at 70℃; for 3h; Inert atmosphere;		83%
487041-08-7

(5R)-3-(3-fluoro-4-iodo-phenyl)-5-hydroxymethyl-1,3-oxazolidin-2-one

1056039-83-8

2-(2-methyl-2H-tetrazol-5-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate In water; N,N-dimethyl-formamide at 90℃; for 6h; Catalytic behavior; Reagent/catalyst; Temperature; Suzuki Coupling; Sealed tube; Inert atmosphere; Green chemistry;77.6%

(5R)-3-[3-fluoro-4-(tributylstannyl)phenyl]-5-(hydroxymethyl)-1,3-oxazolidin-2-one

380380-64-3

5-bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine

856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; lithium chloride In N,N-dimethyl-formamide at 90℃; for 4h; Temperature; Reagent/catalyst;48%
With lithium chloride; bis-triphenylphosphine-palladium(II) chloride In 1-methyl-pyrrolidin-2-one at 20 - 120℃; for 4h;26%
With bis-triphenylphosphine-palladium(II) chloride; lithium chloride In 1-methyl-pyrrolidin-2-one at 120℃; for 4h; Stille coupling; Inert atmosphere;26%
With bis-triphenylphosphine-palladium(II) chloride; lithium chloride at 120℃; for 4h;
624-28-2

2,5-dibromopyridine

856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sodium cyanide / N,N-dimethyl-formamide / 7 h / 150 °C / Inert atmosphere
2: sodium azide; ammonium chloride / N,N-dimethyl-formamide / 3 h / 110 °C / Inert atmosphere
3: sodium hydroxide / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere
4: bis-triphenylphosphine-palladium(II) chloride; lithium chloride / 1-methyl-pyrrolidin-2-one / 4 h / 120 °C / Inert atmosphere
View Scheme
97483-77-7

2-Cyano-5-bromopyridine

856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium azide; ammonium chloride / N,N-dimethyl-formamide / 3 h / 110 °C / Inert atmosphere
2: sodium hydroxide / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere
3: bis-triphenylphosphine-palladium(II) chloride; lithium chloride / 1-methyl-pyrrolidin-2-one / 4 h / 120 °C / Inert atmosphere
View Scheme
372-19-0

meta-fluoroaniline

856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodium hydrogencarbonate / tetrahydrofuran / 2 h / 0 °C
2.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -78 °C / Inert atmosphere
2.2: 26 h / -78 - 20 °C / Inert atmosphere
3.1: N-iodo-succinimide; trifluoroacetic acid / 3 h / 20 °C
4.1: potassium carbonate; palladium diacetate / N,N-dimethyl-formamide; water / 6 h / 90 °C / Sealed tube; Inert atmosphere; Green chemistry
View Scheme
Multi-step reaction with 5 steps
1: ethanol / 12 h / Reflux
2: triethylamine / N,N-dimethyl-formamide / 4 h / 65 °C
3: trifluorormethanesulfonic acid; N-iodo-succinimide / dichloromethane / 2 h / 0 °C
4: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 4 h
5: lithium chloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 4 h / 90 °C
View Scheme
Multi-step reaction with 7 steps
1.1: sodium hydrogencarbonate / dichloromethane / 20 - 25 °C / Inert atmosphere
2.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -65 - -60 °C / Inert atmosphere
2.2: 20 h / -65 - 25 °C / Inert atmosphere
3.1: trifluoroacetic acid; N-iodo-succinimide / 0.17 h / 20 - 25 °C
3.2: 4 h / 20 - 25 °C
4.1: dmap / toluene / 7 h / 45 - 50 °C
5.1: tris-(o-tolyl)phosphine; potassium carbonate / dimethyl sulfoxide / 20 - 25 °C / Inert atmosphere
5.2: 5.17 h / 20 - 85 °C / Inert atmosphere
6.1: sodium azide; ammonium chloride / N,N-dimethyl-formamide / 4 h / 95 - 100 °C / Inert atmosphere
7.1: triphenylphosphine; diethylazodicarboxylate / dichloromethane / 5 h / 20 - 25 °C / Inert atmosphere
7.2: 3 h / 20 - 25 °C
View Scheme

3-[3-Fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)-3-pyridinyl]phenyl]-5-(hydroxymethyl)-2-oxazolidinone Chemical Properties

Molecular structure of 3-[3-Fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)-3-pyridinyl]phenyl]-5-(hydroxymethyl)-2-oxazolidinone (CAS NO.856866-72-3) is:

Product Name: 3-[3-Fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)-3-pyridinyl]phenyl]-5-(hydroxymethyl)-2-oxazolidinone
CAS Registry Number: 856866-72-3
Molecular Formula: C17H15FN6O3
Molecular Weight: 370.34
Density: 1.57 g/cm3
Classification Code: Antibiotic

3-[3-Fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)-3-pyridinyl]phenyl]-5-(hydroxymethyl)-2-oxazolidinone Specification

 3-[3-Fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)-3-pyridinyl]phenyl]-5-(hydroxymethyl)-2-oxazolidinone , its cas register number is 856866-72-3. It also can be called Torezolid [USAN] ; Torezolid ;  (5R)-3-(3-fluoro-4-(6-(2-methyl-2H-tetrazol-5-yl)pyridin-3-yl)phenyl)-5-(hydroxymethyl)oxazolidin-2-one ;  2-Oxazolidinone, 3-(3-fluoro-4-(6-(2-methyl-2H-tetrazol-5-yl)-3-pyridinyl)phenyl)-5-(hydroxymethyl)-, (5R)- .It is an oxazolidinone drug in phase-II clinical trials for complicated skin and skin-structure infections (cSSSI), including those caused by Methicillin-resistant Staphylococcus aureus (MRSA).

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