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LIDE PHARMACEUTICALS LIMITED

Advantage : LIDE PHARMACEUTICALS LTD. is a mid-small manufacturing-type enterprise, engaged in pharmaceutical intermediates of R&D, custom-made and production, and also involving trading chemicals for export. We have established the R&amp

Remdesivir/ LIDE PHARMA- Factory supply / Best price

Cas:1809249-37-3

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Xi'an Xszo Chem Co., Ltd.

1. Factory price and high quality must be guaranteed, base on 8 years of production and R&D experience2. Free samples will be provided,ensure specifications and quality are right for customer3. Customers will receive the most professional technical s

High Quality 99% Remdesivir 1809249-37-3 GMP Manufacturer

Cas:1809249-37-3

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Sinoway Industrial Co., Ltd.

Why is SINOWAY: 1) Specialized in pharmaceutical and healthcare industrial for 34 years. 2) ISO 9001:2015 & SGS audited supplier . 3) Accept various payment terms : T.T 30-60 days. 4) We have warehouse in USA with quickly shipment . 5) We c

High purity 99% factory price in stock Remdesivir powder

Cas:1809249-37-3

Min.Order:1 Kilogram

FOB Price: $15.0 / 500.0

Type:Trading Company

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Hangzhou JINLAN Pharm-Drugs Technology Co., Ltd

Jinlan Pharm-Drugs Technology Co.,Limited (with its export company Hangzhou Royall Import & Export Co.,Ltd.)is located in Hangzhou, Zhejiang Province. Neighboring Ningbo port, Shanghai port, Hangzhou Xiaoshan Int’l Airport and Shanghai Pu

1809249-37-3/Remdesivir API

Cas:1809249-37-3

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Henan Kanbei Chemical Co.,LTD

1. Well-equipped, stable and high-quality raw material supply chain, to provide customers with the best quality products. 2.Strict quality inspection process and professional certificate testing to ensure the quality level of the final product. 3.E

hot sale remdesivir

Cas:1809249-37-3

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Hangzhou Maytime Bio-Tech Co.,Ltd.

WE HAVE FINISHED LAB TRIAL ,PILOT TRIAL ,VALIDITY BATCH IS AROUND 10KGS . Appearance:white to off-white powder Storage:store in sealed container ,keep from light Application:antiviral drug Port:any port in China

Remdesivir

Cas:1809249-37-3

Min.Order:0 Metric Ton

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Hangzhou Think Chemical Co. Ltd

Remdesivir Intermediate 2-C-(4-Aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-2,5-anhydro-D-altrononitrile CAS:1191237-69-0 Remdesivir CAS:1809249-37-3 Appearance:detailed see specifications Storage:Stored in a cool a

High purity Remdesivir and Intermediate stock

Cas:1809249-37-3

Min.Order:100 Gram

FOB Price: $2.0

Type:Other

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Enke Pharma-tech Co.,Ltd. (Cangzhou, China )

Cangzhou Enke Pharma Tech Co.,ltd. is located in Cangzhou City, Hebei province ,where is a famous petroleum chemical industry city in China. Enke Pharma a high-tech enterprise ,and we are dedicated to developing and manufacturing

GS 5734

Cas:1809249-37-3

Min.Order:1 Kilogram

FOB Price: $10.0

Type:Manufacturers

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Hebei yanxi chemical co.,LTD.

1. Best quality in your requirement 2. Competitive price in China market 3. mature Technical support 4. Professional logistic support 5 . Full experience of large numbers containers loading in Chinese sea port 6 Fast shipment by reputed s

Remdesivir

Cas:1809249-37-3

Min.Order:1 Kilogram

FOB Price: $1.0 / 2.0

Type:Trading Company

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Hubei DiBo chemical co., LTD

Name:Remdesivir CAS NO:1809249-37-3 Grade:Pharmaceutical raw materials Product Quality 12 years of chemical raw materials Mature operation of the industry System stability Data storage Security without vulnerability Product Technology S

Remdesivir CAS:1809249-37-3 Chinese manufacturers high-quality

Cas:1809249-37-3

Min.Order:25 Kilogram

FOB Price: $1.0 / 2.0

Type:Other

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Hebei Nengqian Chemical Import and Export Co., LTD

With our good experience, we offer detailed technical support and advice to assist customers. We communicate closely with customers to establish their quality requirements. Consistent Quality Our plant has strict quality control in each manufacturin

Antiviral Drug Remdesivi CAS 1809249-37-3

Cas:1809249-37-3

Min.Order:1 Kilogram

FOB Price: $10.0 / 16.0

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Henan Sinotech Import&Export Corporation

Name: Remdesiver CasNo:1809249-37-3 Molecular Formula:C27H35N6O8P Purity:USP40,98%~102% Molecular Weight:602.58 Appearance:White Powder Storage:Store in cool and dry place, away from sun light. Package:25kg Application: API Transportation:By sea

Remdesiver

Cas:1809249-37-3

Min.Order:1 Kilogram

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Hangzhou Sartort Biopharma Co., Ltd

Appearance:White solid powder Storage:Room temperature Package:25kg/drum Application:Coronavirus;Covid-19 Transportation:Express/Sea/Air Port:Any port in China

In stock High Purity Coronavirus Covid-19 Remdesivir powder for API

Cas:1809249-37-3

Min.Order:1 Kilogram

FOB Price: $11500.0 / 12500.0

Type:Lab/Research institutions

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HANWAYS CHEMPHARM CO.,LIMITED

Hanways Chempharm Co., Limited, the former is Hubei Hanways Pharchem CO.,Limited, set up in 2009 in Wuhan, China. We specialize in sourcing and supplying APIs, pharmaceutical intermediates, and fine chemicals for worldwide markets. The founder has d

Pharmaceutical Raw Material Remdesivir

Cas:1809249-37-3

Min.Order:1 Kilogram

FOB Price: $1.0

Type:Trading Company

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Qingdao Beluga Import and Export Co., LTD

Beluga chemical professional supply Remdesivir 1809249-37-3 Why choose Beluga chemical 1. Beluga Chemical has a professional RESEARCH and development team and strong technical force to ensure technical support and research capabilities. 2. Made

Remdesivir

Cas:1809249-37-3

Min.Order:1 Kilogram

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Wuhan Wonda Pharm Limited

1.high quality: quality is life. quality is the most important element for all goods. we have a lab doing research in wuhan china. hplc and nmr is available if needed. 2.reasonable price: we provide high quality products with competi

Covid-19 High Purity cas 1809249-37-3 Remdesivir powder

Cas:1809249-37-3

Min.Order:10 Gram

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Henan Wentao Chemical Product Co., Ltd.

Henan Wentao Chemical Product Co.,Ltd is Located in Zhengzhou High-tech Development Zone with import and export license, We passed ISO 9001:2008 as well, Henan Wentao has developed more than 1000 compounds, which are widely used in the fields of prod

Remdesivir

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Hebei Mojin Biotechnology Co.,Ltd

Hebei Mojin Biotechnology Co., Ltd,Our business covers more than 30 countries, most of the big customers come from Europe, America and other countries in the world, we can guarantee the quality and price. In recent decades, with the efforts of all em

Remdesivir CAS 1809249-37-3

Cas:1809249-37-3

Min.Order:1 Gram

FOB Price: $500.0

Type:Trading Company

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Hubei Yuanmeng Biological Technology Co., Ltd.

Hubei Yuanmeng Biological Technology Co., Ltd., which is located in Wuhan, China. We are specializing in the exportation of APIs, and plant extracts ect. Our products has been exported to America, Australia, Brazil, the Europe, Middle East and other

99% Remdesivir CAS 1809249-37-3 with Best Price

Cas:1809249-37-3

Min.Order:1 Kilogram

FOB Price: $7.0 / 11.0

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Afine Chemicals Limited

Company Introduction 1. Established in 2005, with two independent business divisions: Fine chemicals division; Pharmaceutical division. 2. Main product: Optical brightener Textile auxiliary Dye stuff Pigments

REMDESIVIR

Cas:1809249-37-3

Min.Order:1 Gram

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Hebei Miheng Trading Co., Ltd.

Remdesivir CAS 1809249-37-3 Our advantage 1.Top quality: Using high quality material and establishing a strict quality control system,assigning specific persons in charge of each part of production,from raw material purchase to assembly. 2

Remdesivir CAS 1809249-37-3

Cas:1809249-37-3

Min.Order:1 Kilogram

FOB Price: $10.0 / 50.0

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Hangzhou Fonlynn Health Technology Co., Ltd.

Packing: According to customer requirements Delivery time: In stock or depands Port of shipment: Ningbo/Shanghai/Qingdao OEM/ODM:Welcome Sample:We can offer our existing samples at once Transportation:Express/Sea/Air Port:Ningbo/Shanghai/Qingd

Remdesivir

Cas:1809249-37-3

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Shanghai Hope Chem Co., Ltd

1. Product advantages: exquisite appearance and unique functions. 2. Product Advantages: Our products are the best,fast speed ,in large stock 3. High-quality products and thoughtful service are your greatest satisfaction. 4. The product

High Purity ,stock, Remdesivir CAS:1809249-37-3

Cas:1809249-37-3

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Shaanxi New nine Material Technology Co., Ltd.

Our Advantage: 1. Rich experience We specialize in this filed for many years, our APIs exported to all over the world and and we established long friendly relations of cooperation with our clients. 2. Great quality,purity and favorable Good quali

Remdesivir

Cas:1809249-37-3

Min.Order:1 Kilogram

FOB Price: $10.0 / 100.0

Type:Trading Company

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Hefei Zhaobo Technology Co., Ltd.

Remdesivir CAS 1809249-37-3 Purity: 99% Min Application: Intermediates Appearance: Powder Package: Bag Delivery: 3-5days Our Advantage & Service 1.Top quality: Using high quality material and establishing a strict quality control sys

Remdesivir CAS 1809249-37-3

Cas:1809249-37-3

Min.Order:1 Kilogram

FOB Price: $10.0 / 50.0

Type:Trading Company

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SHANGHAI SYSTEAM BIOCHEM CO., LTD

Remdesivir instock (We can supply this product in high purity and the Various intermediates ) We are specialized in custom synthesis, chemical/pharmaceutical/ pesticides outsourcing and contract research. We are committed to

Remdesivir

Cas:1809249-37-3

Min.Order:1 Gram

FOB Price: $1.0

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Wuxi TAA Chemical Industry Co.,LTD.

1.A strong technical force and advanced processing equipments. The quality of the products has been strictly inspected and all kinds of index have reached or exceeded domestic and international standards. 2. Now we have established long-term stabl

High quality Remdesivir for hot sale

Cas:1809249-37-3

Min.Order:1 Kilogram

FOB Price: $1.0

Type:Other

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Zibo Hangyu Biotechnology Development Co., Ltd

Zibo Hangyu Biotechnology Development Co., Ltd is a leading manufacturer and supplier of chemicals in China. We develop produce and distribute high quality pharmaceuticals, intermediates, special chemicals and OLED intermediates and other fine chemi

cas:1809249-37-3

Cas:1809249-37-3

Min.Order:10 Gram

Negotiable

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Siwei Development Group Ltd.

Product name: Remdesivir(CAS:1809249-37-3) CAS No.:1809249-37-3 Molecule Formula:C27H35N6O8P Molecule Weight:602.58 Purity: 99.0% Package: 25kg/drum Description:White powder Manufacture Standards:Enterprise Standard

Best Quality Remdesivir(CAS:1809249-37-3)

Cas:1809249-37-3

Min.Order:1 Kilogram

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Henan Tianfu Chemical Co., Ltd.

Our company was built in 2009 with an ISO certificate.In the past 5 years, we have grown up as a famous fine chemicals supplier in China and we had established stable business relationships with Samsung, LG, Merck, Thermo Fisher Scientific and so o

1809249-37-3

Cas:1809249-37-3

Min.Order:1 Metric Ton

FOB Price: $1.0

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Synthetic route

2-ethylbutyl ((S)-(((3aR,4R,6R,6aR)-6-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-6-cyano-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate

2-ethylbutyl ((S)-(((3aR,4R,6R,6aR)-6-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-6-cyano-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
With hydrogenchloride In water; acetone at 20℃; for 3h; pH=3 - 4; Reagent/catalyst;91%
With hydrogenchloride In tetrahydrofuran; water at 0 - 25℃; for 8h;73%
With hydrogenchloride In tetrahydrofuran; water at 20℃; Inert atmosphere;69%
(2R,3R,4S,5R)‑2‑(4‑aminopyrrolo[1,2‑f][1,2,4]triazin‑7‑yl)‑3,4‑dihydroxy‑5‑(hydroxymethyl)tetrahydrofuran‑2‑carbonitrile
1191237-69-0

(2R,3R,4S,5R)‑2‑(4‑aminopyrrolo[1,2‑f][1,2,4]triazin‑7‑yl)‑3,4‑dihydroxy‑5‑(hydroxymethyl)tetrahydrofuran‑2‑carbonitrile

C21H26N3O9P

C21H26N3O9P

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
Stage #1: (2R,3R,4S,5R)‑2‑(4‑aminopyrrolo[1,2‑f][1,2,4]triazin‑7‑yl)‑3,4‑dihydroxy‑5‑(hydroxymethyl)tetrahydrofuran‑2‑carbonitrile With titanium(IV) isopropylate; tert-butylmagnesium chloride In tetrahydrofuran at -10 - 0℃; for 0.5h;
Stage #2: C21H26N3O9P In tetrahydrofuran at -10 - 20℃; Solvent; Reagent/catalyst;
86.2%
2-ethylbutyl (2S)-2-{[(S)-{[(3aR,4R,6R,6aR)-6-{4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl}-6-cyano-2-phenyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-yl]methoxy}(phenoxy)phosphoryl]amino}propanoate

2-ethylbutyl (2S)-2-{[(S)-{[(3aR,4R,6R,6aR)-6-{4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl}-6-cyano-2-phenyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-yl]methoxy}(phenoxy)phosphoryl]amino}propanoate

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
at 60℃;84%
(2R,3R,4S,5R)‑2‑(4‑aminopyrrolo[1,2‑f][1,2,4]triazin‑7‑yl)‑3,4‑dihydroxy‑5‑(hydroxymethyl)tetrahydrofuran‑2‑carbonitrile
1191237-69-0

(2R,3R,4S,5R)‑2‑(4‑aminopyrrolo[1,2‑f][1,2,4]triazin‑7‑yl)‑3,4‑dihydroxy‑5‑(hydroxymethyl)tetrahydrofuran‑2‑carbonitrile

C19H27N2O7P

C19H27N2O7P

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
With diisopropylamine; zinc dibromide In tetrahydrofuran at 20℃; for 4h; Reagent/catalyst; Solvent; Inert atmosphere; Molecular sieve;81%
2-ethylbutyl (2S)-2-{[chloro(phenoxy)phosphoryl]amino}propanoate
1355049-92-1

2-ethylbutyl (2S)-2-{[chloro(phenoxy)phosphoryl]amino}propanoate

(3αR,4R,6R,6αR)-4-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carbonitrile
1191237-80-5

(3αR,4R,6R,6αR)-4-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carbonitrile

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
Stage #1: (3αR,4R,6R,6αR)-4-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carbonitrile With 2,6-dimethylpyridine; C17H21N3O2 In dichloromethane at -20 - 20℃; for 0.333333h; Inert atmosphere; Molecular sieve;
Stage #2: 2-ethylbutyl (2S)-2-{[chloro(phenoxy)phosphoryl]amino}propanoate In dichloromethane at -20 - 20℃; for 24h; Inert atmosphere; Molecular sieve;
Stage #3: With toluene-4-sulfonic acid In methanol at 20℃; for 24h; Inert atmosphere;
73%
Multi-step reaction with 2 steps
1.1: C17H21N3O2; 2,6-dimethylpyridine / dichloromethane / 0.33 h / -40 - 20 °C / Inert atmosphere; Molecular sieve
1.2: 24 h / 4 - 20 °C / Inert atmosphere; Molecular sieve
2.1: hydrogenchloride / tetrahydrofuran; water / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1.1: C17H21N3O2; 2,6-dimethylpyridine / dichloromethane / 0.33 h / -40 - 20 °C / Inert atmosphere; Molecular sieve
1.2: 24 h / 4 - 20 °C / Inert atmosphere; Molecular sieve
2.1: hydrogenchloride / tetrahydrofuran; water / 20 °C / Inert atmosphere
View Scheme
Stage #1: (3αR,4R,6R,6αR)-4-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carbonitrile With tert-butylmagnesium chloride In tetrahydrofuran at -40 - 30℃;
Stage #2: 2-ethylbutyl (2S)-2-{[chloro(phenoxy)phosphoryl]amino}propanoate In tetrahydrofuran at -40 - 10℃;
100 mg
(2R,3R,4S,5R)‑2‑(4‑aminopyrrolo[1,2‑f][1,2,4]triazin‑7‑yl)‑3,4‑dihydroxy‑5‑(hydroxymethyl)tetrahydrofuran‑2‑carbonitrile
1191237-69-0

(2R,3R,4S,5R)‑2‑(4‑aminopyrrolo[1,2‑f][1,2,4]triazin‑7‑yl)‑3,4‑dihydroxy‑5‑(hydroxymethyl)tetrahydrofuran‑2‑carbonitrile

C20H26ClN2O5P

C20H26ClN2O5P

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
With triethylamine; zinc(II) chloride In tetrahydrofuran at 65℃; for 25h; Inert atmosphere;44%
(2R,3R,4S,5R)‑2‑(4‑aminopyrrolo[1,2‑f][1,2,4]triazin‑7‑yl)‑3,4‑dihydroxy‑5‑(hydroxymethyl)tetrahydrofuran‑2‑carbonitrile
1191237-69-0

(2R,3R,4S,5R)‑2‑(4‑aminopyrrolo[1,2‑f][1,2,4]triazin‑7‑yl)‑3,4‑dihydroxy‑5‑(hydroxymethyl)tetrahydrofuran‑2‑carbonitrile

C20H26ClN2O5P

C20H26ClN2O5P

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; magnesium chloride In 1,4-dioxane at 55℃; for 25h; Inert atmosphere;42%
(2R,3R,4S,5R)‑2‑(4‑aminopyrrolo[1,2‑f][1,2,4]triazin‑7‑yl)‑3,4‑dihydroxy‑5‑(hydroxymethyl)tetrahydrofuran‑2‑carbonitrile
1191237-69-0

(2R,3R,4S,5R)‑2‑(4‑aminopyrrolo[1,2‑f][1,2,4]triazin‑7‑yl)‑3,4‑dihydroxy‑5‑(hydroxymethyl)tetrahydrofuran‑2‑carbonitrile

C20H26BrN2O5P

C20H26BrN2O5P

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
With potassium carbonate; zinc dibromide In tert-butyl methyl ether at 75℃; for 25h; Inert atmosphere;40.5%
(2R,3R,4R,5R)-2-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-bis((tert-butyldimethylsilyl)oxy)-5-(hydroxymethyl)tetrahydrofuran-2-carbonitrile

(2R,3R,4R,5R)-2-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-bis((tert-butyldimethylsilyl)oxy)-5-(hydroxymethyl)tetrahydrofuran-2-carbonitrile

(2S)-2-ethylbutyl 2-(((S)-(perfluorophenoxy)(phenoxy)phosphoryl)amino)propanoate

(2S)-2-ethylbutyl 2-(((S)-(perfluorophenoxy)(phenoxy)phosphoryl)amino)propanoate

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tert-butylmagnesium chloride / tetrahydrofuran / 16 h / -10 - 5 °C
2: hydrogenchloride; water / 72 h / 0 - 20 °C
View Scheme
(2R,3R,4R,5R)-2-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-bis((tert-butyldimethylsilyl)oxy)-5-(hydroxymethyl)tetrahydrofuran-2-carbonitrile

(2R,3R,4R,5R)-2-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-bis((tert-butyldimethylsilyl)oxy)-5-(hydroxymethyl)tetrahydrofuran-2-carbonitrile

2-ethylbutyl (2S)-2-((S)-((4-nitrophenoxy)(phenoxy)phosphoryl)amino)propanoate

2-ethylbutyl (2S)-2-((S)-((4-nitrophenoxy)(phenoxy)phosphoryl)amino)propanoate

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: magnesium chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 21 h / 50 °C
2: hydrogenchloride; water / 72 h / 0 - 20 °C
View Scheme
(S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-bis((tertbutyldimethylsilyl)oxy)-5-cyanotetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

(S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-bis((tertbutyldimethylsilyl)oxy)-5-cyanotetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
With hydrogenchloride; water at 0 - 20℃; for 72h;
(3R,4R,5R)-2-(4-aminopyrrole-[2,1-f][1,2,4]-triazin-7-yl)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-ol
1355049-94-3

(3R,4R,5R)-2-(4-aminopyrrole-[2,1-f][1,2,4]-triazin-7-yl)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-ol

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: dichloromethane / 0.17 h / -78 °C / Inert atmosphere
1.2: 1 h / -78 °C / Inert atmosphere
2.1: boron trichloride / dichloromethane / 1 h / -78 - -20 °C / Inert atmosphere
3.1: magnesium chloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 5 h / 30 °C
View Scheme
Multi-step reaction with 3 steps
1.1: dichloromethane / 0.17 h / -78 °C / Inert atmosphere
1.2: 1 h / -78 °C / Inert atmosphere
2.1: boron trichloride / dichloromethane / 1 h / -78 - -20 °C / Inert atmosphere
3.1: magnesium chloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 6 h / 30 °C
View Scheme
Multi-step reaction with 3 steps
1.1: dichloromethane / 0.17 h / -78 °C / Inert atmosphere
1.2: 1 h / -78 °C / Inert atmosphere
2.1: boron trichloride / dichloromethane / 1 h / -78 - -20 °C / Inert atmosphere
3.1: tert-butylmagnesium chloride / tetrahydrofuran; N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere
View Scheme
(3R,4R,5R)-2-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-bis(benzyloxy)-5-((benzyloxy) methyl)tetrahydrofuran-2-carbonitrile
1191237-68-9

(3R,4R,5R)-2-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-bis(benzyloxy)-5-((benzyloxy) methyl)tetrahydrofuran-2-carbonitrile

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: boron trichloride / dichloromethane / 1 h / -78 - -20 °C / Inert atmosphere
2: magnesium chloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 5 h / 30 °C
View Scheme
Multi-step reaction with 2 steps
1: boron trichloride / dichloromethane / 1 h / -78 - -20 °C / Inert atmosphere
2: magnesium chloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 6 h / 30 °C
View Scheme
Multi-step reaction with 2 steps
1: boron trichloride / dichloromethane / 1 h / -78 - -20 °C / Inert atmosphere
2: tert-butylmagnesium chloride / tetrahydrofuran; N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere
View Scheme
(2R,3R,4S,5R)‑2‑(4‑aminopyrrolo[1,2‑f][1,2,4]triazin‑7‑yl)‑3,4‑dihydroxy‑5‑(hydroxymethyl)tetrahydrofuran‑2‑carbonitrile
1191237-69-0

(2R,3R,4S,5R)‑2‑(4‑aminopyrrolo[1,2‑f][1,2,4]triazin‑7‑yl)‑3,4‑dihydroxy‑5‑(hydroxymethyl)tetrahydrofuran‑2‑carbonitrile

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sulfuric acid / acetone / 0.5 h / 45 °C
2: magnesium chloride; N-ethyl-N,N-diisopropylamine / acetonitrile / 4 h / 20 °C
3: hydrogenchloride; water / tetrahydrofuran / 0 - 20 °C
View Scheme
Multi-step reaction with 4 steps
1: acetone / 0.5 h / 20 °C
2: potassium carbonate / water; ethyl acetate
3: magnesium chloride; N-ethyl-N,N-diisopropylamine / acetonitrile / 4 h / 20 °C
4: hydrogenchloride; water / tetrahydrofuran / 0 - 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: sulfuric acid / acetone / 0.5 h / 45 °C
2.1: magnesium chloride / acetonitrile / 0.25 h / 20 °C
2.2: 4 h
3.1: water; hydrogenchloride / tetrahydrofuran / 0 - 20 °C
View Scheme
(2R,3R,4S,5R)‑2‑(4‑aminopyrrolo[1,2‑f][1,2,4]triazin‑7‑yl)‑3,4‑dihydroxy‑5‑(hydroxymethyl)tetrahydrofuran‑2‑carbonitrile
1191237-69-0

(2R,3R,4S,5R)‑2‑(4‑aminopyrrolo[1,2‑f][1,2,4]triazin‑7‑yl)‑3,4‑dihydroxy‑5‑(hydroxymethyl)tetrahydrofuran‑2‑carbonitrile

(2S)-2-ethylbutyl 2-(((4-nitrophenoxy)(phenoxy)phosphoryl)amino)propanoate
1439900-56-7

(2S)-2-ethylbutyl 2-(((4-nitrophenoxy)(phenoxy)phosphoryl)amino)propanoate

A

(2S)-2-ethylbutyl 2-(((R)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

(2S)-2-ethylbutyl 2-(((R)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

B

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
With tert-butylmagnesium chloride In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere;
Multi-step reaction with 2 steps
1: tert-butylmagnesium chloride / N,N-dimethyl-formamide; tetrahydrofuran / 2.17 h / 20 °C / Inert atmosphere
2: Lux Cellulose-2 / acetonitrile; methanol / Resolution of racemate
View Scheme
(2R,3R,4S,5R)‑2‑(4‑aminopyrrolo[1,2‑f][1,2,4]triazin‑7‑yl)‑3,4‑dihydroxy‑5‑(hydroxymethyl)tetrahydrofuran‑2‑carbonitrile
1191237-69-0

(2R,3R,4S,5R)‑2‑(4‑aminopyrrolo[1,2‑f][1,2,4]triazin‑7‑yl)‑3,4‑dihydroxy‑5‑(hydroxymethyl)tetrahydrofuran‑2‑carbonitrile

(2S)-2-ethylbutyl 2-(((S)-(perfluorophenoxy)(phenoxy)phosphoryl)amino)propanoate

(2S)-2-ethylbutyl 2-(((S)-(perfluorophenoxy)(phenoxy)phosphoryl)amino)propanoate

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; magnesium chloride In N,N-dimethyl acetamide at 30℃; for 5h;
(2R,3R,4S,5R)‑2‑(4‑aminopyrrolo[1,2‑f][1,2,4]triazin‑7‑yl)‑3,4‑dihydroxy‑5‑(hydroxymethyl)tetrahydrofuran‑2‑carbonitrile
1191237-69-0

(2R,3R,4S,5R)‑2‑(4‑aminopyrrolo[1,2‑f][1,2,4]triazin‑7‑yl)‑3,4‑dihydroxy‑5‑(hydroxymethyl)tetrahydrofuran‑2‑carbonitrile

2-ethylbutyl (2S)-2-((S)-((4-nitrophenoxy)(phenoxy)phosphoryl)amino)propanoate

2-ethylbutyl (2S)-2-((S)-((4-nitrophenoxy)(phenoxy)phosphoryl)amino)propanoate

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; magnesium chloride In N,N-dimethyl acetamide at 30℃; for 6h;
4-amino-7-iodopyrrolo[2,1-f ][1,2,4]triazine
1770840-43-1

4-amino-7-iodopyrrolo[2,1-f ][1,2,4]triazine

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: chloro-trimethyl-silane / tetrahydrofuran / 0.5 h / 0 °C
1.2: 0.58 h / 0 - 5 °C
2.1: dichloromethane / 0.17 h / -78 °C / Inert atmosphere
2.2: 1 h / -78 °C / Inert atmosphere
3.1: boron trichloride / dichloromethane / 1 h / -78 - -20 °C / Inert atmosphere
4.1: tert-butylmagnesium chloride / tetrahydrofuran; N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1.1: chloro-trimethyl-silane / tetrahydrofuran / 0.5 h / 0 °C
1.2: 0.58 h / 0 - 5 °C
2.1: dichloromethane / 0.17 h / -78 °C / Inert atmosphere
2.2: 1 h / -78 °C / Inert atmosphere
3.1: boron trichloride / dichloromethane / 1 h / -78 - -20 °C / Inert atmosphere
4.1: magnesium chloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 5 h / 30 °C
View Scheme
Multi-step reaction with 4 steps
1.1: chloro-trimethyl-silane / tetrahydrofuran / 0.5 h / 0 °C
1.2: 0.58 h / 0 - 5 °C
2.1: dichloromethane / 0.17 h / -78 °C / Inert atmosphere
2.2: 1 h / -78 °C / Inert atmosphere
3.1: boron trichloride / dichloromethane / 1 h / -78 - -20 °C / Inert atmosphere
4.1: magnesium chloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 6 h / 30 °C
View Scheme
(2R,3R,4R,5R)‐2‐{4‐aminopyrrolo[2,1‐f][1,2,4]triazin‐7‐yl}‐3,4‐bis(benzyloxy)‐5‐[(benzyloxy)methyl]tetrahydrofuran‐2‐carbonitrile
1355357-49-1

(2R,3R,4R,5R)‐2‐{4‐aminopyrrolo[2,1‐f][1,2,4]triazin‐7‐yl}‐3,4‐bis(benzyloxy)‐5‐[(benzyloxy)methyl]tetrahydrofuran‐2‐carbonitrile

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: boron trichloride / dichloromethane / 1 h / -20 - -15 °C
2: magnesium chloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 5 h / 30 °C
View Scheme
Multi-step reaction with 2 steps
1: boron trichloride / dichloromethane / 1 h / -20 - -15 °C
2: magnesium chloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 6 h / 30 °C
View Scheme
Multi-step reaction with 2 steps
1: boron trichloride / dichloromethane / 1 h / -20 - -15 °C
2: tert-butylmagnesium chloride / tetrahydrofuran; N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere
View Scheme
O-phenyl phosphorodichloridate
770-12-7

O-phenyl phosphorodichloridate

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: triethylamine / Isopropyl acetate / 1 h / -20 °C
1.2: 1.5 h
2.1: magnesium chloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 6 h / 30 °C
View Scheme
Multi-step reaction with 2 steps
1.1: triethylamine / dichloromethane / 1.5 h / -15 °C / Inert atmosphere
1.2: 2 h
2.1: magnesium chloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 5 h / 30 °C
View Scheme
Multi-step reaction with 3 steps
1.1: triethylamine / Isopropyl acetate / 1 h / -20 °C
1.2: 1.5 h
2.1: magnesium chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 21 h / 50 °C
3.1: hydrogenchloride; water / 72 h / 0 - 20 °C
View Scheme
4-aminopyrrolo[2,1-f][1,2,4]triazine
159326-68-8

4-aminopyrrolo[2,1-f][1,2,4]triazine

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: N-iodo-succinimide / N,N-dimethyl-formamide / 3 h / 0 °C
2.1: chloro-trimethyl-silane / tetrahydrofuran / 0.5 h / 0 °C
2.2: 0.58 h / 0 - 5 °C
3.1: trimethylsilyl trifluoromethanesulfonate; trifluoroacetic acid / dichloromethane / 0.17 h / -40 - -25 °C
4.1: boron trichloride / dichloromethane / 1 h / -20 - -15 °C
5.1: magnesium chloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 5 h / 30 °C
View Scheme
Multi-step reaction with 5 steps
1.1: N-iodo-succinimide / N,N-dimethyl-formamide / 3 h / 0 °C
2.1: chloro-trimethyl-silane / tetrahydrofuran / 0.5 h / 0 °C
2.2: 0.58 h / 0 - 5 °C
3.1: trimethylsilyl trifluoromethanesulfonate; trifluoroacetic acid / dichloromethane / 0.17 h / -40 - -25 °C
4.1: boron trichloride / dichloromethane / 1 h / -20 - -15 °C
5.1: magnesium chloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 6 h / 30 °C
View Scheme
Multi-step reaction with 5 steps
1.1: N-iodo-succinimide / N,N-dimethyl-formamide / 3 h / 0 °C
2.1: chloro-trimethyl-silane / tetrahydrofuran / 0.5 h / 0 °C
2.2: 0.58 h / 0 - 5 °C
3.1: dichloromethane / 0.17 h / -78 °C / Inert atmosphere
3.2: 1 h / -78 °C / Inert atmosphere
4.1: boron trichloride / dichloromethane / 1 h / -78 - -20 °C / Inert atmosphere
5.1: tert-butylmagnesium chloride / tetrahydrofuran; N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere
View Scheme
2-ethylbutyl (S)-2-aminopropanoate hydrochloride
946511-97-3

2-ethylbutyl (S)-2-aminopropanoate hydrochloride

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: triethylamine / Isopropyl acetate / 1 h / -20 °C
1.2: 1.5 h
2.1: magnesium chloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 6 h / 30 °C
View Scheme
Multi-step reaction with 2 steps
1.1: triethylamine / dichloromethane / 1.5 h / -15 °C / Inert atmosphere
1.2: 2 h
2.1: magnesium chloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 5 h / 30 °C
View Scheme
Multi-step reaction with 3 steps
1.1: triethylamine / Isopropyl acetate / 1 h / -20 °C
1.2: 1.5 h
2.1: magnesium chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 21 h / 50 °C
3.1: hydrogenchloride; water / 72 h / 0 - 20 °C
View Scheme
(3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-dihydro-furan-2-one
14233-64-8, 134307-32-7, 55094-52-5

(3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-dihydro-furan-2-one

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: chloro-trimethyl-silane / tetrahydrofuran / 0.33 h / 20 °C / Inert atmosphere
1.2: 0.17 h / -78 °C / Inert atmosphere
2.1: dichloromethane / 0.17 h / -78 °C / Inert atmosphere
2.2: 1 h / -78 °C / Inert atmosphere
3.1: boron trichloride / dichloromethane / 1 h / -78 - -20 °C / Inert atmosphere
4.1: tert-butylmagnesium chloride / tetrahydrofuran; N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1.1: chloro-trimethyl-silane / tetrahydrofuran / 0.33 h / 20 °C / Inert atmosphere
1.2: 0.17 h / -78 °C / Inert atmosphere
2.1: dichloromethane / 0.17 h / -78 °C / Inert atmosphere
2.2: 1 h / -78 °C / Inert atmosphere
3.1: boron trichloride / dichloromethane / 1 h / -78 - -20 °C / Inert atmosphere
4.1: magnesium chloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 5 h / 30 °C
View Scheme
Multi-step reaction with 4 steps
1.1: chloro-trimethyl-silane / tetrahydrofuran / 0.33 h / 20 °C / Inert atmosphere
1.2: 0.17 h / -78 °C / Inert atmosphere
2.1: dichloromethane / 0.17 h / -78 °C / Inert atmosphere
2.2: 1 h / -78 °C / Inert atmosphere
3.1: boron trichloride / dichloromethane / 1 h / -78 - -20 °C / Inert atmosphere
4.1: magnesium chloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 6 h / 30 °C
View Scheme
2-ethylbutyl (2S)-2-((S)-((4-nitrophenoxy)(phenoxy)phosphoryl)amino)propanoate

2-ethylbutyl (2S)-2-((S)-((4-nitrophenoxy)(phenoxy)phosphoryl)amino)propanoate

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: magnesium chloride; N-ethyl-N,N-diisopropylamine / acetonitrile / 4 h / 20 °C
2: hydrogenchloride; water / tetrahydrofuran / 0 - 20 °C
View Scheme
(3αR,4R,6R,6αR)-4-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carbonitrile
1191237-80-5

(3αR,4R,6R,6αR)-4-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carbonitrile

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: magnesium chloride; N-ethyl-N,N-diisopropylamine / acetonitrile / 4 h / 20 °C
2: hydrogenchloride; water / tetrahydrofuran / 0 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: magnesium chloride / acetonitrile / 0.25 h / 20 °C
1.2: 4 h
2.1: hydrogenchloride / tetrahydrofuran; water / 0 - 20 °C
View Scheme
(3aR,4R,6R,6aR)-4-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carbonitrile p-tolylsulfonic acid salt

(3aR,4R,6R,6aR)-4-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carbonitrile p-tolylsulfonic acid salt

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium carbonate / water; ethyl acetate
2: magnesium chloride; N-ethyl-N,N-diisopropylamine / acetonitrile / 4 h / 20 °C
3: hydrogenchloride; water / tetrahydrofuran / 0 - 20 °C
View Scheme
2,3,5-tri-O-benzyl-D-ribofuranose
16838-89-4

2,3,5-tri-O-benzyl-D-ribofuranose

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: acetic anhydride; dimethyl sulfoxide / 48 h / 20 °C / Inert atmosphere
2.1: chloro-trimethyl-silane / tetrahydrofuran / 0.33 h / 20 °C / Inert atmosphere
2.2: 0.17 h / -78 °C / Inert atmosphere
3.1: dichloromethane / 0.17 h / -78 °C / Inert atmosphere
3.2: 1 h / -78 °C / Inert atmosphere
4.1: boron trichloride / dichloromethane / 1 h / -78 - -20 °C / Inert atmosphere
5.1: tert-butylmagnesium chloride / tetrahydrofuran; N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1.1: acetic anhydride; dimethyl sulfoxide / 48 h / 20 °C / Inert atmosphere
2.1: chloro-trimethyl-silane / tetrahydrofuran / 0.33 h / 20 °C / Inert atmosphere
2.2: 0.17 h / -78 °C / Inert atmosphere
3.1: dichloromethane / 0.17 h / -78 °C / Inert atmosphere
3.2: 1 h / -78 °C / Inert atmosphere
4.1: boron trichloride / dichloromethane / 1 h / -78 - -20 °C / Inert atmosphere
5.1: magnesium chloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 5 h / 30 °C
View Scheme
Multi-step reaction with 5 steps
1.1: acetic anhydride; dimethyl sulfoxide / 48 h / 20 °C / Inert atmosphere
2.1: chloro-trimethyl-silane / tetrahydrofuran / 0.33 h / 20 °C / Inert atmosphere
2.2: 0.17 h / -78 °C / Inert atmosphere
3.1: dichloromethane / 0.17 h / -78 °C / Inert atmosphere
3.2: 1 h / -78 °C / Inert atmosphere
4.1: boron trichloride / dichloromethane / 1 h / -78 - -20 °C / Inert atmosphere
5.1: magnesium chloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 6 h / 30 °C
View Scheme
2-ethylbutyl (2S)-2-((S)-((4-nitrophenoxy)(phenoxy)phosphoryl)amino)propanoate

2-ethylbutyl (2S)-2-((S)-((4-nitrophenoxy)(phenoxy)phosphoryl)amino)propanoate

(3αR,4R,6R,6αR)-4-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carbonitrile
1191237-80-5

(3αR,4R,6R,6αR)-4-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carbonitrile

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: magnesium chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 50 °C
2: hydrogenchloride / tetrahydrofuran; water / 0 °C
View Scheme
With N-ethyl-N,N-diisopropylamine; magnesium chloride In tetrahydrofuran at 20℃; for 3h; Temperature;
Multi-step reaction with 2 steps
1: magnesium chloride; N-ethyl-N,N-diisopropylamine / acetonitrile / 50 °C / Inert atmosphere
2: hydrogenchloride / tetrahydrofuran; water / 20 °C / Inert atmosphere
View Scheme
4-amino-7-iodopyrrolo[2,1-f ][1,2,4]triazine
1770840-43-1

4-amino-7-iodopyrrolo[2,1-f ][1,2,4]triazine

A

(2S)-2-ethylbutyl 2-(((R)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

(2S)-2-ethylbutyl 2-(((R)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

B

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: chloro-trimethyl-silane; phenylmagnesium chloride / tetrahydrofuran / 0.5 h / 0 - 5 °C / Inert atmosphere
1.2: 0.17 h / -15 - -12 °C
1.3: 1 h / -20 °C
2.1: dichloromethane / 0.17 h / 0 °C / Inert atmosphere
2.2: 1 h / 0 °C
3.1: boron trichloride / dichloromethane / 1 h / -78 °C / Inert atmosphere
4.1: 1-methyl-1H-imidazole / tetrahydrofuran / 0 °C / Inert atmosphere
5.1: Lux Cellulose-2 chiral column / acetonitrile; methanol / Resolution of racemate
View Scheme
Multi-step reaction with 5 steps
1.1: chloro-trimethyl-silane; phenylmagnesium chloride / tetrahydrofuran / 0.5 h / 0 - 5 °C / Inert atmosphere
1.2: 0.17 h / -15 - -12 °C
1.3: 1 h / -20 °C
2.1: dichloromethane / 0.17 h / 0 °C / Inert atmosphere
2.2: 1 h / 0 °C
3.1: boron trichloride / dichloromethane / 1 h / -78 °C / Inert atmosphere
4.1: tert-butylmagnesium chloride / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / 20 °C
5.1: Lux Cellulose-2 chiral column / acetonitrile; methanol / Resolution of racemate
View Scheme
Multi-step reaction with 5 steps
1.1: chloro-trimethyl-silane; phenylmagnesium chloride / tetrahydrofuran / 0.5 h / 0 - 5 °C / Inert atmosphere
1.2: 0.17 h / -15 - -12 °C
1.3: 1 h / -20 °C
2.1: dichloromethane / 0.17 h / 0 °C / Inert atmosphere
2.2: 1 h / 0 °C
3.1: boron trichloride / dichloromethane / 1 h / -78 °C / Inert atmosphere
4.1: tert-butylmagnesium chloride / tetrahydrofuran; N,N-dimethyl-formamide / 2.17 h / Inert atmosphere
5.1: Lux Cellulose-2 chiral column / acetonitrile; methanol / Resolution of racemate
View Scheme
O-phenyl phosphorodichloridate
770-12-7

O-phenyl phosphorodichloridate

A

(2S)-2-ethylbutyl 2-(((R)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

(2S)-2-ethylbutyl 2-(((R)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

B

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: triethylamine / dichloromethane / 4 h / -78 °C / Inert atmosphere
1.2: 4 h / 0 - 20 °C
2.1: tert-butylmagnesium chloride / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / 20 °C
3.1: Lux Cellulose-2 chiral column / acetonitrile; methanol / Resolution of racemate
View Scheme
Multi-step reaction with 3 steps
1.1: triethylamine / dichloromethane / 4 h / -78 - 20 °C
1.2: 4 h / 0 - 20 °C
2.1: tert-butylmagnesium chloride / N,N-dimethyl-formamide; tetrahydrofuran / 1 h
3.1: Lux Cellulose-2 / acetonitrile; methanol / Resolution of racemate
View Scheme
(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
1809249-37-3

(2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

((((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)oxidophosphoryl)alanine bis-sodium salt

((((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)oxidophosphoryl)alanine bis-sodium salt

Conditions
ConditionsYield
With sodium hydroxide In water; acetonitrile for 2h;

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