[ CAS No. 946075-13-4 ] {[proInfo.proName]}

Name: 946075-13-4|1-((2R,3R)-3-(4-(4-Cyanophenyl)thiazol-2-yl)-2-(2,5-difluorophenyl)-2-hydroxybutyl)-4-(1-((methyl(3-(((methylglycyl)oxy)methyl)pyridin-2-yl)carbamoyl)oxy)ethyl)-1H-1,2,4-triazol-4-ium hydrogen sulfate|98%
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SKU: A599121
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Quality Control of [ 946075-13-4 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 946075-13-4 ]

CAS No. :	946075-13-4	MDL No. :	MFCD27987905
Formula :	C₃₅H₃₆F₂N₈O₉S₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LWXUIUUOMSMZKJ-KLFWAVJMSA-M
M.W :	814.84	Pubchem ID :	72196309
Synonyms :	BAL8557-002;Isavuconazonium (sulfate)	Chemical Name :	1-((2R,3R)-3-(4-(4-Cyanophenyl)thiazol-2-yl)-2-(2,5-difluorophenyl)-2-hydroxybutyl)-4-(1-((methyl(3-(((methylglycyl)oxy)methyl)pyridin-2-yl)carbamoyl)oxy)ethyl)-1H-1,2,4-triazol-4-ium hydrogen sulfate

Safety of [ 946075-13-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 946075-13-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 946075-13-4 ]

[ 946075-13-4 ] Synthesis Path-Downstream 1~10

1
[ CAS Unavailable ]
[ 946075-13-4 ]

Yield	Reaction Conditions	Operation in experiment
	With strong anion exchange resin (sulfate) In methanol; water at 0 - 5℃;	4 Example-4: Synthesis of 1-[[N-methyl-N-3-[(methylamino)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 Sulfate Dissolved 10.0 g 1-[[N-methyl-N-3-[(methylamino)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 hydrochloride in 200 ml deminerahzed water and 30 ml methanol. The solution was cooled to about 0 to 5°C. The strong anion exchange resin (sulfate) was added to the cooled solution. The reaction mixture was stirred to about 60-80 minutes. The reaction was filtered and washed with 50ml of demineralized water and methylene chloride. The aqueous layer was lyophilized to obtain (8.0 g) white solid. Yield: 93 % HPLC Purity: > 90% Mass: m/z 717.4 (M-HS04) +

Reference： [1]Current Patent Assignee: WOCKHARDT LIMITED - WO2016/16766, 2016, A2 Location in patent: Page/Page column 15

2
[ 497235-79-7 ]
[ 946075-13-4 ]

Yield	Reaction Conditions	Operation in experiment
76%	Stage #1: isavuconazonium chloride With sodium hydrogencarbonate In water at 0℃; Stage #2: With sulfuric acid; dihydrogen peroxide In methanol; water at -5℃; for 0.5h;	1 Example 1 Preparation of isavuconazonium sulfate crystalline form Isavuconazonium chloride 0.9g (1mmol) was dissolved in 9 ml water. Lower the temperature to 0 °C. Use aqueous solution of sodium bicarbonate for adjusting pH to 7. Add 9 ml dichloromethane and extract. After separating tha liquid layers, dry and concentrate. Afterwards, add 10 ml methanol to dissolve. Lower the temperature to -5 °C. Separately drop 0.09g (1mmol) of concentrated sulfuric acid and 0.11g (1mmol) 30% aqueous hydrogen peroxide solution. Stir for 30min. concentrated, adding 5 ml 95% ethanol and 5 ml ethyl acetate recrystallized, heating to 40 °C dissolved, stirring and cooling to 20 °C, crystallization, filtration, vacuum drying to obtain 0.62g white solid, yield 76%, purity 97.6%,

Reference： [1]Current Patent Assignee: SINO BIOPHARMACEUTICAL LIMITED - CN106565699, 2017, A Location in patent: Paragraph 0037-0047

3
[ 241479-67-4 ]
1-[[N-methyl-N-3-[(methylamino)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 sulfate [ No CAS ]

Reference： [1]Patent: CN110128420,2019,A
[2]Patent: CN110128420,2019,A

4
[ 338990-31-1 ]
[ 946075-13-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: sodium iodide / acetonitrile / 12 h / 50 - 60 °C / Inert atmosphere 2: hydrogensulfate/sulfate type anion exchange resin / ethanol; water / 1 h / 25 °C 3: sulfuric acid / water / 2 h / 0 - 30 °C
	Multi-step reaction with 3 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 3: hydrogen sulfate-based anion exchange resin / water / 0.5 h / 20 °C / Large scale
	Multi-step reaction with 4 steps 1: sodium iodide / acetonitrile / 50 - 60 °C 2: dichloromethane; water / 20 °C 3: acetonitrile; dichloromethane; water / 0 - 30 °C 4: sodium hydrogen sulfate / dichloromethane; water / 0 - 10 °C

Reference： [1]Current Patent Assignee: Yin Qiming;Li Jia;Mao Jun;Zhou Weihai - CN110128420, 2019, A
[2]Current Patent Assignee: Yin Qiming;Li Jia;Mao Jun;Zhou Weihai - CN110128420, 2019, A
[3]Current Patent Assignee: SHANGHAI DESANO CHEMICAL PHARMACEUTICAL CO.; SHANGHAI DESANO BIO-PHARMACEUTICAL CO.; SHANGHAI DESANO PHARMACEUTICALS CO. - US2023/75632, 2023, A1

5
[ 338990-64-0 ]
[ 946075-13-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sulfuric acid / ethyl acetate; ethanol / 1 h / 30 °C / Reflux; Large scale 2: hydrogen sulfate-based anion exchange resin / water / 0.5 h / 20 °C / Large scale
75.96 %	With sulfuric acid In ethanol Large scale;	1-3 Example 2 Step 1: get the iodonium salt (the compound of structure shown in formula I) of 10.70kg isavuconazolium,Dissolve in 42.26kg of absolute ethanol, add a mixed solution of sulfuric acid (1.24kg) and ethanol (4.73kg), stir for 2 hours to remove tert-butoxycarbonyl, remove the solvent in vacuo, and collect the precipitate.Step 2: Fully dissolve the precipitate in step 1 with a mixed solution of ethyl acetate (57kg) and water (31.4kg), extract and remove impurities for the first time, collect the water phase, and then use ethyl acetate to carry out the first step on the water phase. Secondary extraction was performed to remove impurities, and the aqueous phase was collected, which was recorded as the first aqueous phase.Step 3: Add the first water phase in step 2 to the reaction kettle and mix it with 21.4kg of styrene-based hydrogen sulfate anion exchange resin, control the temperature to 25°C ± 5°C, stir for 0.5h, suction filtration until no liquid flows out, and collect the filtrate , and then add 21.4kg/kg of styrene-based hydrogen sulfate anion exchange resin to the filtrate, control the temperature to 25±5, stir and react for 0.5h, take out the lower layer of the aqueous phase and check the residual iodide ion <0.1%, then suction filtration, An aqueous solution of isavuconazole sulfate was obtained, which was designated as the second aqueous phase.Step 4: Add DCM (26.5kg) to the second aqueous phase in step 3 for extraction and removal of impurities, collect the aqueous phase after layering, record it as the third aqueous phase, and freeze the third aqueous phase to obtain isha sulfate Conazole (5.25 kg, 75.96% yield).The purity of isavuconazole sulfate detected by HPLC was 98.3%.The isavuconazole sulfate obtained in this example is detected by HPLC external standard method: the glacial acetic acid residue is unqualified (the glacial acetic acid content in this example is 0.66%, which is greater than the 0.5% required by the pharmacopoeia standard).
	Multi-step reaction with 3 steps 1: dichloromethane; water / 20 °C 2: acetonitrile; dichloromethane; water / 0 - 30 °C 3: sodium hydrogen sulfate / dichloromethane; water / 0 - 10 °C

Reference： [1]Current Patent Assignee: Yin Qiming;Li Jia;Mao Jun;Zhou Weihai - CN110128420, 2019, A
[2]Current Patent Assignee: YANGTZE RIVER PHARMACEUTICAL GROUP CO LTD - CN115215857, 2022, A Location in patent: Paragraph 0078-0100
[3]Current Patent Assignee: SHANGHAI DESANO CHEMICAL PHARMACEUTICAL CO.; SHANGHAI DESANO BIO-PHARMACEUTICAL CO.; SHANGHAI DESANO PHARMACEUTICALS CO. - US2023/75632, 2023, A1

6
[ CAS Unavailable ]
[ 946075-13-4 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen sulfate-based anion exchange resin In water at 20℃; for 0.5h; Large scale;	5-7 Example 5Preparation of the compound of formula 3 Adding 1 kg of an aqueous solution of the compound of formula 4 and 2.50 Kg of a hydrogen sulfate-based anion exchange resin to the double-layer glass reactor to start mechanical stirring.The reaction was stirred at a temperature of 20±5° C. for 0.5 h, suction filtration, and the filter cake was rinsed with 0.90 Kg of ethyl acetate.After suction filtration until no liquid flows out, the filtrate is collected.2.50 kg of hydrogen sulfate-based sulfate anion exchange resin was added again to the filtrate.The temperature is controlled at 20±5°C, the reaction is stirred for 0.5h, and suction filtration is performed.The filter cake was rinsed with 0.90 Kg of ethyl acetate and suction filtered until no liquid flowed out.The mixture was stirred for 10 min, and the organic phase was separated.The aqueous phase was again washed with 2.66 Kg×3 of DCM and stirred for 10 min each time.The aqueous phase was collected, extracted with 0.68 Kg×3 n-heptane extraction, and stirred for 10 min each time.The aqueous phase is collected and the aqueous phase is lyophilized to give the compound of formula 3,That is, oxaconazole sulfate.

Reference： [1]Current Patent Assignee: Yin Qiming;Li Jia;Mao Jun;Zhou Weihai - CN110128420, 2019, A Location in patent: Paragraph 0014; 0028-0030

7
[ CAS Unavailable ]
[ 946075-13-4 ]

Yield	Reaction Conditions	Operation in experiment
57%	With sulfuric acid In water at 0 - 30℃; for 2h;	11-12 Example 11Preparation of the compound of formula 3 To a 250 ml three-neck round bottom reaction flask, the compound of the formula 6 (6 g) prepared in Example 10, EA (20 ml), purified water (10 ml) was sequentially added.Stir and cool to 0 ° C in an ice water bath at an internal temperature of 0-10 ° C. 2M H2SO4 in EA (3.5 ml) was added dropwise to the solution.After the completion of the dropwise addition, the temperature was raised to 30 ° C and stirred for 2 h;The reaction system is cooled to 15 ° C,Add 30 ml of purified water to the reaction flask.Add 100ml EA and stir at room temperature for 15min.Let stand layering. The separated aqueous phase was washed successively with 30 ml of EA, 30 ml of DCM and 10 ml of Heptane; the resulting aqueous phase was freeze-dried.Obtaining 3g of a white to pale yellow solid;The yield was 57% and the HPLC purity was >98%.

Reference： [1]Current Patent Assignee: Yin Qiming;Li Jia;Mao Jun;Zhou Weihai - CN110128420, 2019, A Location in patent: Paragraph 0014; 0034-0035

8
[ 2399419-65-7 ]
[ 946075-13-4 ]

Yield	Reaction Conditions	Operation in experiment
71.3%	In methanol at 0 - 20℃; for 3h;	4 Synthesis of A6: Add 150mL of anhydrous methanol to a 1L three-necked flask,Compound A5 (12.2g), stirred at room temperature until dissolved, and cooled in an ice-water bath to an internal temperature below 0 ° C.75 g of sulfuric acid resin was added, and the reaction was stirred and exchanged at 0 to 5 ° C for 3 hours.Suction filtration, the solid was washed once with 50mL of methanol,The filtrate was concentrated under reduced pressure at 30 ° C, and the remaining solid was dissolved by stirring with 36 mL of absolute ethanol. 108 mL of isopropanol was added under stirring, and the mixture was stirred at room temperature for 2 hours.Nitrogen protection and suction filtration, the solid was washed with isopropyl alcohol 10mL × 2,The obtained solid was decompressed under vacuum at room temperature for 12 hours,8.5g of off-white solid,Yield: 71.3%. Purity by HPLC showed 99.3%.

Reference： [1]Current Patent Assignee: BEIJING LUNARSUN PHARMACEUTICAL - CN110551064, 2019, A Location in patent: Paragraph 0129; 0133-0134

9
[ CAS Unavailable ]
[ 946075-13-4 ]

Yield	Reaction Conditions	Operation in experiment
50%	With strongly basic styrene-based anion exchange resin In dichloromethane; water at 15℃; for 1h; Inert atmosphere;	3-6 After washing the ion exchange resin with deionized water, acid washing and alkali washing, add 1mol/L sodium bisulfate solution to soak for 4h, filter, and wash the resin with water until the filtrate is neutral to prepare styrene hydrogen sulfate anion exchange resin .The ion exchange resin is a strongly basic styrene-based anion exchange resin, which is a 719 product of Aladdin Technology Company, and the exchange capacity of the 719 ion exchange resin is 1.4 mmol/ml;Add 45 grams of compound 6 to a mixture of 1500ml of dichloromethane and 10ml of deionized water. Under the protection of nitrogen, add 656ml of the ion exchange resin mentioned above, stir at 15 for 1h, separate the liquids, collect the upper aqueous layer, and add dichloride Washed twice with 50ml of methane, lyophilized to obtain a white powder, which is said 1-[3-(R)-[4-(4-cyanophenyl)thiazol-2-yl]-(2R)-( 2,5-Difluorophenyl)-2-hydroxybutyl-4-[1-[N-methyl-N-[3-[2-(methylamino)acetoxymethyl]pyridin-2-yl ]Carbamyloxy]ethyl]-1H-1,2,4-triazolium sulfate (compound 1)

Reference： [1]Current Patent Assignee: CHINA NATIONAL PHARMACEUTICAL GROUP CORPORATION - CN112279846, 2021, A Location in patent: Paragraph 0057-0085

10
[ 2618686-19-2 ]
[ 946075-13-4 ]

Yield	Reaction Conditions	Operation in experiment
91.7 %	With sodium hydrogen sulfate In dichloromethane; water at 0 - 10℃;	6-8 Example 6 Preparation of Isavuconazonium Sulfate 40.0 g (0.04 mol) of compound of formula V was dissolved in 200 ml of dichloromethane solution, then 300 ml of 20 wt % sodium bisulfate aqueous solution (0.5 mol) was added, and stirred at 010° C. until the compound V was completely converted (the conversion time was 0.51 hour). The mixture was liquid separated and the aqueous phase was extracted with dichloromethane and n-heptane respectively. (0168) The aqueous phase was adsorbed by macroporous resin to remove inorganic small molecule salts, and eluted twice with 200 ml*2 acetone. The eluent was collected and combined, concentrated to remove the organic phase in the eluent, and the remaining aqueous phase after concentration was lyophilized to obtain 31.6 g of isavuconazonium sulfate (91.7% yield, 99.89% purity).

Reference： [1]Current Patent Assignee: SHANGHAI DESANO CHEMICAL PHARMACEUTICAL CO.; SHANGHAI DESANO BIO-PHARMACEUTICAL CO.; SHANGHAI DESANO PHARMACEUTICALS CO. - US2023/75632, 2023, A1 Location in patent: Paragraph 0166-0174

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A1325872[ 742049-41-8 ]

1-((2R,3R)-3-(4-(4-cyanophenyl)thiazol-2-yl)-2-(2,5-difluorophenyl)-2-hydroxybutyl)-4-(1-((methyl(3-(((methylglycyl)oxy)methyl)pyridin-2-yl)carbamoyl)oxy)ethyl)-1H-1,2,4-triazol-4-ium

Reason: Free-salt

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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
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H281	Contains refrigerated gas; may cause cryogenic burns or injury
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H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
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H316	Causes mild skin irritation
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H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
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Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 946075-13-4 ] {[proInfo.proName]}

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[ 946075-13-4 ] Synthesis Path-Downstream 1~10

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