Isavuconazole supplier | CasNO.241479-67-4

Name
Isavuconazole
EINECS 1592732-453-0
CAS No. 241479-67-4
Article Data9
CAS DataBase
Density 1.38 g/cm³
Solubility
Melting Point
Formula C₂₂H₁₇F₂N₅OS
Boiling Point 678 °C at 760 mmHg
Molecular Weight 437.473
Flash Point 363.8 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 4-[2-[(1R,2R)-2-(2,5-Difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-4-thiazolyl]benzonitrile;Benzonitrile, 4-[2-[(1R,2R)-2-(2,5-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-4-thiazolyl]-;
PSA 115.86000
LogP 4.24298

Synthetic route

: isavuconazole hydrobromide

: 241479-67-4
Isavuconazole

Conditions

Conditions	Yield
With sodium hydrogencarbonate In ethyl acetate	92.6%

: (2R,3R)-3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)butanethioamide

: 20099-89-2
4-Cyanophenacyl bromide

: 241479-67-4
Isavuconazole

Conditions

Conditions	Yield
With sodium hydrogencarbonate In ethanol	86%
In ethanol at 60 - 65℃; for 15h;	81.6%
In ethanol at 78℃; for 3h;	77.4%
In ethanol at 70℃;

: 20099-89-2
4-Cyanophenacyl bromide

: C13H19FN4OS

: 241479-67-4
Isavuconazole

Conditions

Conditions	Yield
In ethanol at 60℃; for 2h;	70%

: 241479-74-3
(2S,3R)-3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)butyronitrile

: 241479-67-4
Isavuconazole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hydrogen sulfide; sulfuric acid / ethanol / 5 h / Autoclave; Heating 2.1: ethanol / 8 h / 60 - 70 °C 2.2: 5 h / 20 - 70 °C / pH 4 - 5 View Scheme
Multi-step reaction with 2 steps 1: O,O-Diethyl hydrogen phosphorodithioate / water / 6 h / 78 °C 2: ethanol / 3 h / 78 °C View Scheme
Multi-step reaction with 2 steps 1: diammonium sulfide / tetrahydrofuran / 96 h / 27 - 30 °C / Reflux 2: ethanol / 15 h / 60 - 65 °C View Scheme

: (2R,3R)-3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)thiobutyramide hydrogensulphate

: 40805-50-3
4-(2-chloroacetyl)benzenecarbonitrile

: 241479-67-4
Isavuconazole

Conditions

Conditions	Yield
Stage #1: (2R,3R)-3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)thiobutyramide hydrogensulphate; 4-(2-chloroacetyl)benzenecarbonitrile In ethanol at 60 - 70℃; for 8h; Stage #2: With triethylamine In ethanol; water at 20 - 70℃; for 5h; pH=4 - 5;

: 3-[4-(4-cyanophenyl)thiazol-2-yl]-1-(1H-1,2,4-triazol-1-yl)-2-(2,5-difluorophenyl)-butan-2-ol

: 241479-67-4
Isavuconazole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid / toluene / 20 - 70 °C 2: sodium hydrogencarbonate / dichloromethane; water View Scheme

: (2R,3R)-3-[4-(4-cyanophenyl)thiazol-2-yl]-1-(1H-1,2,4-triazol-1-yl)-2-(2,5-difluorophenyl)-butan-2-ol (1R)-10-camphorsulfonate

: 241479-67-4
Isavuconazole

Conditions

Conditions	Yield
With sodium hydrogencarbonate In dichloromethane; water

: 3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)butanenitrile

: 241479-67-4
Isavuconazole

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: acetone; methanol / 20 °C / Reflux 2.1: sodium hydroxide / dichloromethane; water 3.1: hydrogen sulfide; sulfuric acid / ethanol / 5 h / Autoclave; Heating 4.1: ethanol / 8 h / 60 - 70 °C 4.2: 5 h / 20 - 70 °C / pH 4 - 5 View Scheme

: (2S,3R)-3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)butanenitrile-(1R)-10-camphorsulfonate

: 241479-67-4
Isavuconazole

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydroxide / dichloromethane; water 2.1: hydrogen sulfide; sulfuric acid / ethanol / 5 h / Autoclave; Heating 3.1: ethanol / 8 h / 60 - 70 °C 3.2: 5 h / 20 - 70 °C / pH 4 - 5 View Scheme

: (2R,3R)-3-[4-(4-cyanophenyl)thiazol-2-yl]-1-(1H-1,2,4-triazol-1-yl)-2-(2,5-difluorophenyl)-butan-2-ol hydrobromide

: 241479-67-4
Isavuconazole

Conditions

Conditions	Yield
With sodium hydrogencarbonate In dichloromethane; water	18.5 g

: 60468-36-2
α-chloro-2',5'-difluoroacetophenone

: 241479-67-4
Isavuconazole

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: triphenylphosphine; dichloro bis(acetonitrile) palladium(II) / tetrahydrofuran / 0.17 h / -20 °C / Inert atmosphere 1.2: 3 h / -10 °C 2.1: sodium carbonate / dimethyl sulfoxide / 4 h / 70 °C 3.1: [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid / toluene; tert-butyl methyl ether; methanol / 1 h / 60 °C 4.1: O,O-Diethyl hydrogen phosphorodithioate / water / 6 h / 78 °C 5.1: ethanol / 3 h / 78 °C View Scheme

Yield

Multi-step reaction with 5 steps
1.1: triphenylphosphine; dichloro bis(acetonitrile) palladium(II) / tetrahydrofuran / 0.17 h / -20 °C / Inert atmosphere
1.2: 3 h / -10 °C
2.1: sodium carbonate / dimethyl sulfoxide / 4 h / 70 °C
3.1: [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid / toluene; tert-butyl methyl ether; methanol / 1 h / 60 °C
4.1: O,O-Diethyl hydrogen phosphorodithioate / water / 6 h / 78 °C
5.1: ethanol / 3 h / 78 °C
View Scheme

: C11H10ClF2NO

: 241479-67-4
Isavuconazole

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium carbonate / dimethyl sulfoxide / 4 h / 70 °C 2: [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid / toluene; tert-butyl methyl ether; methanol / 1 h / 60 °C 3: O,O-Diethyl hydrogen phosphorodithioate / water / 6 h / 78 °C 4: ethanol / 3 h / 78 °C View Scheme

: 1157938-97-0
1-(2,5-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone

: 241479-67-4
Isavuconazole

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere 1.2: 0.33 h 1.3: 2 h / -50 °C 2.1: [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid / toluene; tert-butyl methyl ether; methanol / 1 h / 60 °C 3.1: O,O-Diethyl hydrogen phosphorodithioate / water / 6 h / 78 °C 4.1: ethanol / 3 h / 78 °C View Scheme
Multi-step reaction with 4 steps 1.1: indium / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 1.2: 10 h / -10 °C 2.1: [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid / toluene; tert-butyl methyl ether; methanol / 1 h / 60 °C 3.1: O,O-Diethyl hydrogen phosphorodithioate / water / 6 h / 78 °C 4.1: ethanol / 3 h / 78 °C View Scheme

: 3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl) butyronitrile

: 241479-67-4
Isavuconazole

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid / toluene; tert-butyl methyl ether; methanol / 1 h / 60 °C 2: O,O-Diethyl hydrogen phosphorodithioate / water / 6 h / 78 °C 3: ethanol / 3 h / 78 °C View Scheme

: 338990-31-1
N-methyl N-(3-[((N-tert-butoxycarbonyl-N-methylamino)acetoxy)methyl]pyridin-2-yl)carbamic acid (1-chloroethyl) ester

: 241479-67-4
Isavuconazole

: 1-[[N-methyl-N-3-[(t-butoxycarbonylmethylamino)acetoxymethyl]pyridin-2-yl]carbamoyloxy]ethyl-1-[(2R,3R)-2-(2,5-difluorophenyl)-2-hydroxy-3-[4-(4-cyanophenyl)thiazol-2-yl]butyl]-1H-[1,2,4]-triazo-4-ium iodide

Conditions

Conditions	Yield
With sodium iodide In acetonitrile at 70℃; for 3h; Inert atmosphere;	98%
With sodium iodide In acetonitrile at 45 - 50℃; for 15h;	88.4%
With sodium iodide In acetonitrile at 50 - 60℃; for 12h; Reagent/catalyst; Temperature; Inert atmosphere;	83%

: 338990-23-1
2(S)-[acetoxymethyl]-1-[chloromethyloxycarbonyl]pyrrolidine

: 241479-67-4
Isavuconazole

: [[2(S)-(acetoxymethyl)pyrrolidin-1-yl]carbonyloxy]methyl-1-[(2R,3R)-2-(2,5-difluorophenyl)-2-hydroxy-3-[4-(4-cyanophenyl)thiazol-2-yl]butyl]-1H-[1,2,4]triazol-4-ium iodide

Conditions

Conditions	Yield
With sodium iodide In acetonitrile at 50℃;	92%

: 338990-31-1
N-methyl N-(3-[((N-tert-butoxycarbonyl-N-methylamino)acetoxy)methyl]pyridin-2-yl)carbamic acid (1-chloroethyl) ester

: 241479-67-4
Isavuconazole

: C40H43F2N8O7S(1+)*Br(1-)

Conditions

Conditions	Yield
With tetrabutylammomium bromide; sodium bromide In acetonitrile at 25 - 30℃; for 48h; Reagent/catalyst; Temperature;	89.2%

: 338990-56-0
[N-ethyl-N-(tert-butoxycarbonylethylamino)ethyl]carbamic acid 1-chloroethyl ester

: 241479-67-4
Isavuconazole

: 1-[[N-ethyl-N-2-(t-butoxycarbonylethylamino)ethyl]carbamoyloxy]ethyl-1-[(2R,3R)-2-(2,5-difluorophenyl)-2-hydroxy-3-[4-(4-cyanophenyl)thiazol-2-yl]butyl]-1H-[1,2,4]triazol-4-ium chloride

Conditions

Conditions	Yield
sodium iodide In acetonitrile at 60℃;	86%

: 4-tert-butoxycarbonyl-methyl-aminoacetoxy-3,5-dimethyl-benzyl bromide

: 241479-67-4
Isavuconazole

: 4-{4-[(tert-Butoxycarbonyl-methyl-amino)-acetoxy]-3,5-dimethyl-benzyl}-1-[(2R,3R)-3-[4-(4-cyano-phenyl)-thiazol-2-yl]-2-(2,5-difluoro-phenyl)-2-hydroxy-butyl]-1H-[1,2,4]triazol-4-ium bromide

Conditions

Conditions	Yield
In acetonitrile	84%

: [N-methyl-N-3-(acetoxy)propyl]carbamic acid chloromethyl ester

: 241479-67-4
Isavuconazole

: [[N-methyl-N-3-(acetoxy)propyl]carbamoyloxy]methyl-1-[(2R,3R)-2-(2,5-difluorophenyl)-2-hydroxy-3-[4-(4-cyanophenyl)thiazol-2-yl]butyl]-1H-[1,2,4]triazol-4-ium iodide

Conditions

Conditions	Yield
With sodium iodide In acetonitrile at 50℃;	82%

: 338990-35-5
[N-methyl-N-2-[(tert-butoxycarbonylmethylamino)acetoxymethyl]-4-fluoro-phenyl]carbamic acid 1-chloroethyl ester

: 241479-67-4
Isavuconazole

: 4-[1-({2-[(tert-butoxycarbonyl-methyl-amino)-acetoxymethyl]-4-fluoro-phenyl}-methyl-carbamoyloxy)-ethyl]-1-[3-[4-(4-cyano-phenyl)-thiazol-2-yl]-2-(2,5-difluoro-phenyl)-2-hydroxy-butyl]-1H-[1,2,4]triazol-4-ium; chloride

Conditions

Conditions	Yield
With sodium iodide In acetonitrile at 70℃;	72%

: 338990-31-1
N-methyl N-(3-[((N-tert-butoxycarbonyl-N-methylamino)acetoxy)methyl]pyridin-2-yl)carbamic acid (1-chloroethyl) ester

: 241479-67-4
Isavuconazole

: 1-[[N-methyl-N-3-[(t-butoxycarbonylmethylamino)acetoxymethyl]pyridin-2-yl]carbamoyloxy]ethyl-1-[(2R,3R)-2-(2,5-difluorophenyl)-2-hydroxy-3-[4-(4-cyanophenyl)thiazol-2-yl]butyl]-1H-[1,2,4]triazol-4-ium chloride

Conditions

Conditions	Yield
With sodium iodide In acetonitrile at 50℃;	65%

: 338990-20-8
[N-methyl-N-2-(acetoxymethyl)phenyl]carbamic acid chloromethyl ester

: 241479-67-4
Isavuconazole

: [[N-methyl-N-2-(acetoxymethyl)phenyl]carbamoyloxy]methyl-1-[(2R,3R)-2-(2,5-difluorophenyl)-2-hydroxy-3-[4-(4-cyanophenyl)thiazol-2-yl]butyl]-1H-[1,2,4]triazol-4-ium chloride

Conditions

Conditions	Yield
With sodium iodide In acetonitrile Heating;	63%
sodium iodide In acetonitrile at 20 - 80℃; for 9h;	63%

: 186353-05-9
[N-methyl-N-phenyl]carbamic acid chloromethyl ester

: 241479-67-4
Isavuconazole

: [[N-methyl-N-phenyl]carbamoyloxy]methyl-1-[(2R,3R)-2-(2,5-difluorophenyl)-2-hydroxy-3-[4-(4-cyanophenyl)thiazol-2-yl]butyl]-1H-[1,2,4]triazol-4-ium chloride

Conditions

Conditions	Yield
In acetonitrile at 80℃;	60%

: 338990-27-5
[N-methyl-N-2-((tert-butoxycarbonylisopropylamino)methyl)phenyl]carbamic acid 1-chloroethyl ester

: 241479-67-4
Isavuconazole

: 338990-62-8
1-[[N-methyl-N-2-(t-butoxycarbonyl-isopropylaminomethyl)phenyl]carbamoyloxy]ethyl-1-[(2R,3R)-2-(2,5-difluorophenyl)-2-hydroxy-3-[4-(4-cyanophenyl)thiazol-2-yl]butyl]-1H-[1,2,4]triazol-4-ium chloride

Conditions

Conditions	Yield
sodium iodide In acetonitrile at 70℃;	51%

: 338990-34-4
[N-methyl-N-2-[(tert-butoxycarbonylmethylamino)acetoxymethyl]-4,5-difluoro-phenyl]carbamic acid 1-chloroethyl ester

: 241479-67-4
Isavuconazole

: 4-[1-({2-[(tert-butoxycarbonyl-methyl-amino)-acetoxymethyl]-4,5-difluoro-phenyl}-methyl-carbamoyloxy)-ethyl]-1-[3-[4-(4-cyano-phenyl)-thiazol-2-yl]-2-(2,5-difluoro-phenyl)-2-hydroxy-butyl]-1H-[1,2,4]triazol-4-ium; chloride

Conditions

Conditions	Yield
With sodium iodide In acetonitrile at 80℃;	50%

: acetic acid 2-(iodomethoxycarbonyl-methyl-amino)-ethyl ester

: 241479-67-4
Isavuconazole

: [[N-methyl-N-2-(acetoxy)ethyl]carbamoyloxy]methyl-1-[(2R,3R)-2-(2,5-difluorophenyl)-2-hydroxy-3-[4-(4-cyanophenyl)thiazol-2-yl]butyl]-1H-[1,2,4]triazol-4-ium iodide

Conditions

Conditions	Yield
In acetonitrile at 50℃;

: 338990-41-3
[N-methyl-N-2-[(tert-butoxycarbonylmethylamino)acetoxymethyl]-5-chlorophenyl]carbamic acid 1-chloroethyl ester

: 241479-67-4
Isavuconazole

: 4-[1-({2-[(tert-butoxycarbonyl-methyl-amino)-acetoxymethyl]-5-chloro-phenyl}-methyl-carbamoyloxy)-ethyl]-1-[3-[4-(4-cyano-phenyl)-thiazol-2-yl]-2-(2,5-difluoro-phenyl)-2-hydroxy-butyl]-1H-[1,2,4]triazol-4-ium; chloride

Conditions

Conditions	Yield
In acetonitrile at 65℃;

: 338990-44-6
[N-methyl-N-2-[(tert-butoxycarbonylmethylamino)acetoxymethyl]-3-fluorophenyl]carbamic acid 1-chloroethyl ester

: 241479-67-4
Isavuconazole

: 4-[1-({2-[(tert-butoxycarbonyl-methyl-amino)-acetoxymethyl]-3-fluoro-phenyl}-methyl-carbamoyloxy)-ethyl]-1-[3-[4-(4-cyano-phenyl)-thiazol-2-yl]-2-(2,5-difluoro-phenyl)-2-hydroxy-butyl]-1H-[1,2,4]triazol-4-ium; chloride

Conditions

Conditions	Yield
With sodium iodide In acetonitrile Heating;

: 241479-67-4
Isavuconazole

: C35H35F2N8O5S(1+)*I(1-)

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium iodide / acetonitrile / 12 h / 50 - 60 °C / Inert atmosphere 2: sulfuric acid / ethyl acetate; ethanol / 1 h / 30 °C / Reflux; Large scale View Scheme

Isavuconazole Specification

The CAS registry number of Isavuconazole is 241479-67-4. The IUPAC name is 4-[2-[(2R,3R)-3-(2,5-difluorophenyl)-3-hydroxy-4-(1,2,4-triazol-1-yl)butan-2-yl]-1,3-thiazol-4-yl]benzonitrile. In addition, the molecular formula is C₂₂H₁₇F₂N₅OS and the molecular weight is 437.46. It should be stored in a cool and dry place.

Physical properties about Isavuconazole are: (1)ACD/LogP: 3.92 ; (2)#H bond acceptors: 6; (3)#H bond donors: 1; (4)#Freely Rotating Bonds: 7; (5)Polar Surface Area: 104.86 Å²; (6)Index of Refraction: 1.665; (7)Molar Refractivity: 117.52 cm³; (8)Molar Volume: 316.2 cm³; (9)Polarizability: 46.59 ×10^-24cm³; (10)Surface Tension: 51.7 dyne/cm; (11)Density: 1.38 g/cm³; (12)Flash Point: 363.8 °C; (13)Enthalpy of Vaporization: 104.54 kJ/mol; (14)Boiling Point: 678 °C at 760 mmHg; (15)Vapour Pressure: 2.61E-19 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: Fc1cc(c(F)cc1)[C@](O)([C@H](c3nc(c2ccc(C#N)cc2)cs3)C)Cn4ncnc4
(2)InChI: InChI=1/C22H17F2N5OS/c1-14(21-28-20(10-31-21)16-4-2-15(9-25)3-5-16)22(30,11-29-13-26-12-27-29)18-8-17(23)6-7-19(18)24/h2-8,10,12-14,30H,11H2,1H3/t14-,22+/m0/s1
(3)InChIKey: DDFOUSQFMYRUQK-RCDICMHDBP

Product Name

Isavuconazole

Synthetic route

Isavuconazole Specification

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