CAS No.856866-72-3,Torezolid Suppliers

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Basic Information

Molecular Structure:
CAS No.:	856866-72-3
Name:	Torezolid
Article Data:	19

Formula:	C₁₇H₁₅FN₆O₃
Molecular Weight:	370.343
Synonyms:	Torezolid
EINECS:	815-370-6
Density:	1.57
Melting Point:	201 °C
Boiling Point:	614.5±65.0 °C(Predicted)
PSA:	106.26000
LogP:	1.46070

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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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%

Yield

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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Yield

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

Conditions	Yield
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

Conditions	Yield
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

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Chemistry

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

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).