1. KDMF is available. 2. Registerred in Iran MOH already. 3. Under registerring in Japan. Hangzhou Huarong Pharm Co., Ltd. established since 2009 , has been always focusing on supplying products and services to our clients in the field of small
We can provide high quality,cheap price,spot supply and good service. If you have any questions,pls do not hesitate to contact us. Hangzhou Hysen pharma CO.,LTD. is a professional Pharmaceutical company. We are specialized in manufacturing and R&am
Cas:608141-41-9
Min.Order:10 Gram
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inquiryDayangchem's R&D center can offer custom synthesis according to the contract research and development services for the fine chemicals, pharmaceutical, biotechnique and some of the other chemicals. DayangChem can provide different quantities
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inquiryItems Standard Result Assay (Ursolic acid) 98%min 98.22% ----------------------------------------------------------------
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Min.Order:1 Gram
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Type:Trading Company
inquiryhebei yanxi chemical co., LTD who registered capital of 10 million yuan, nearly to $2 million, we have a pharmaceutical raw materials factory production of pharmaceutical raw materials, and a reagent r&d center, and we do research and developm
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inquiryUnique advantages for Apremilast Cas 608141-41-9 Guaranteed purity High quality & competitive price Quality control Fast feedback Prompt shipment Appearance:White to off-white powder Storage:N/A Package:1kg/foil bag Application:Medic
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inquiryApremilast CAS No.:608141-41-9 Name: Apremilast Synonyms: CC 10004; (S)-2-[1-(3-Ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione; (S)-N-(2-(1-(3-Ethoxy-4-met
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Min.Order:1 Kilogram
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Type:Other
inquiry1. 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
Cas:608141-41-9
Min.Order:1 Gram
FOB Price: $0.1
Type:Manufacturers
inquiryCangzhou 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 new api, intermedi
Shanghai Seasonsgreen Chemical is a high-tech research and development, production, sale and custom synthesis set in one high-tech chemical products enterprises. Our sales and marketing division is located in Shanghai, serving international pharmaceu
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Min.Order:1 Kilogram
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Type:Manufacturers
inquiryOur main production base is located in Xuzhou industry park. We are certified both to the ISO 9001 and ISO 14001 Standards, have a safety management system in place.Our R&D team masters core technology for process-design of target building block
Chinese Name: Apremilast Chinese alias: (S) - 2 - [1 - (3 - ethoxy - 4 - methoxyphenyl) - 2 - methylsulfonyl ethyl] - 4 - acetylaminoindoline - 1,3 - dione; (S) - 2 - (1 - (3 - ethoxy - 4 - methoxyphenyl) - 2 - methylsulfonyl ethyl) - 4 - acetylam
Cas:608141-41-9
Min.Order:100 Metric Ton
FOB Price: $2.0 / 3.0
Type:Other
inquiryApreMilast Basic information Description Uses Metabolism and Drug interaction safety information side effects References Product Name: ApreMilast Synonyms: (S)-N-(2-(1-(3-Ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl)-1,3-dioxoisoindolin-4-yl
LIDE PHARMACEUTICALS LIMITED is a professional chemicals and APIs leading manufacturer in China. Our core business line covers APIs, Intermediates, Herb extract, etc.
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inquiryTIANFUCHEM-- 608141-41-9--High purity ApreMilast in stock Our company was built in 2009 with an ISO certificate.In the past 10 years, we have grown up as a famous fine chemicals supplier in China And we had established stable business r
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inquiryOur Advantage Rich Experience Our products are sold all over Europe,North&South America, Sino-East, Asia and pacific area as well as Africa,we establish long term. Quality service Company cooperates with research institutes. We strictly con
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inquiryWITH US,YOUR MONEY IN SAFE,YOUR BUSINESS IN SAFE 1)Quick Response Within 12 hours; 2)Quality Guarantee: All products are strictly tested by our QC, confirmed by QA and approved by third party lab in China, USA, Canada, Germany, UK, Italy, France et
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inquiryAppearance:White powder Storage:R.T Package:100G/Bottle, 500G/Bottle, 1KG/Bottle or at customers reqirement. Application:Treat psoriatic arthritis Transportation:Express/Sea/Air Port:Any port in China
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inquiry1. Guaranteed purity; 2. Large quantity in stock; 3. Largest manufacturer; 4. Best service after shipment with email; 5. High quality & competitive price; Appearance:white crystalline powder Storage:Store in sealed containers
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Min.Order:100 Gram
Negotiable
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inquiryProduct Name: Apremilast Synonyms: (S)-N-(2-(1-(3-Ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl)-1,3-dioxoisoindolin-4-yl)acetamide;ApreMilast,CC-10004;brand name: Otezla.;CC10004; CC-10004; CC 10004; APREMILAST; BRAND NAME: OTEZLA.;(S)-4-Ace
About Product Details Items Specifications Test Results Appearance White to white crystalline powde
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Min.Order:1 Gram
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Type:Lab/Research institutions
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Min.Order:1 Gram
Negotiable
Type:Lab/Research institutions
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Min.Order:1 Kilogram
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Type:Lab/Research institutions
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Negotiable
Type:Lab/Research institutions
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inquiryApremilast CAS: 608141-41-9 Specification Item Standard Identification A.H-NMR:Comply with the structure B.LC-MS:Comply with the structure C.The IR spectrum of
4-amino-2-[(1S)-1-(3-ethoxy 4-methoxyphenyl)-2-methanesulfonylethyl]-2,3-dihydro-1H-isoindole-1,3-dione
acetic anhydride
Apremilast
Conditions | Yield |
---|---|
at 135 - 139℃; Large scale; | 98.2% |
at 70℃; for 3h; Inert atmosphere; enantioselective reaction; | 94% |
3-acetylaminophthalic anhydride
(S)-2-[1 (3-ethoxy-4-methoxyphenyl)]-1-methanesulfonyl-2-ethylamine
Apremilast
Conditions | Yield |
---|---|
With acetic acid for 1h; Reflux; Large scale; | 97% |
With acetic acid In acetonitrile at 40℃; for 6h; Reflux; | 94% |
With acetic acid for 3h; Time; Reflux; | 92% |
3-acetylaminophthalic anhydride
(S)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethanamine-(S)-2-acetamido-4-methylpentanoate
Apremilast
Conditions | Yield |
---|---|
With triethylamine In ethyl acetate at 75 - 80℃; for 18h; Reagent/catalyst; Solvent; | 95.1% |
With sodium acetate; acetic acid at 80℃; for 5h; Reagent/catalyst; Temperature; | 91.3% |
Stage #1: (S)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethanamine-(S)-2-acetamido-4-methylpentanoate With sodium hydroxide In dichloromethane at 0 - 5℃; for 2h; Stage #2: 3-acetylaminophthalic anhydride With perchloric acid; acetic acid In dichloromethane at 45℃; for 3.33333h; Reflux; | 89.2% |
3-acetylaminophthalic anhydride
Apremilast
Conditions | Yield |
---|---|
Stage #1: 3-acetylaminophthalic anhydride; (1S)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylthio)ethan-1-amine With acetic acid In acetonitrile for 12h; Reflux; Stage #2: With sodium tungstate (VI) dihydrate; dihydrogen peroxide In acetonitrile at 20℃; for 7h; Cooling; | 94% |
Multi-step reaction with 2 steps 1.1: acetic acid / acetonitrile / 12 h / Reflux 2.1: acetic acid / acetonitrile / 20 °C 2.2: 7 h / 20 °C View Scheme |
Apremilast
Conditions | Yield |
---|---|
Stage #1: N-[2-[(1S)-1-(3-ethoxy-4-methoxyphenyl)(methylthio)ethyl]-2,3-dihydro-1,3-dioxo-1H-isoindol-4-yl]acetamide With acetic acid In acetonitrile at 20℃; Stage #2: With sodium tungstate (VI) dihydrate; dihydrogen peroxide In acetonitrile at 20℃; for 7h; | 91% |
(S)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethanamine-(S)-2-acetamido-4-methylpentanoate
3-acetylaminophthalic acid
Apremilast
Conditions | Yield |
---|---|
With acetic acid at 100 - 120℃; for 2h; Reagent/catalyst; | 86.7% |
With acetic acid at 110 - 115℃; for 1h; | 3.4 g |
Conditions | Yield |
---|---|
With acetic acid for 24h; Time; Reflux; | 85% |
Conditions | Yield |
---|---|
With acetic acid for 24h; Reflux; | 83% |
4-amino-2-[(1S)-1-(3-ethoxy 4-methoxyphenyl)-2-methanesulfonylethyl]-2,3-dihydro-1H-isoindole-1,3-dione
acetyl chloride
Apremilast
Conditions | Yield |
---|---|
With iodine In dichloromethane at 25 - 30℃; | 81% |
With potassium carbonate In ethyl acetate at 25 - 30℃; for 3h; Solvent; Temperature; Concentration; Reflux; | 9 g |
4-amino-2-[(1S)-1-(3-ethoxy 4-methoxyphenyl)-2-methanesulfonylethyl]-2,3-dihydro-1H-isoindole-1,3-dione
acetic anhydride
Apremilast
Conditions | Yield |
---|---|
at 135 - 139℃; Large scale; | 98.2% |
at 70℃; for 3h; Inert atmosphere; enantioselective reaction; | 94% |
at 70℃; for 3h; | 97 %Chromat. |
Conditions | Yield |
---|---|
With chlorobis(ethylene)rhodium(I) dimer; triethylamine In methanol at 60℃; | A 7% B 81% |
With chlorobis(ethylene)rhodium(I) dimer; triethylamine In methanol at 0℃; | A 10% B 7% |
3-acetylaminophthalic anhydride
Apremilast
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 20 - 95℃; for 8h; Concentration; Reagent/catalyst; Temperature; Solvent; | 77% |
3-acetylaminophthalic anhydride
Apremilast
Conditions | Yield |
---|---|
With acetic acid Reflux; | 75% |
2-(3-ethoxy-4-methoxyphenyl)-1-(methylsulfonyl)eth-2-ylamine
3-acetylaminophthalic anhydride
Apremilast
Conditions | Yield |
---|---|
With acetic acid at 50℃; Reflux; | 73.4% |
In acetic acid for 15h; Reflux; | 59% |
Stage #1: 2-(3-ethoxy-4-methoxyphenyl)-1-(methylsulfonyl)eth-2-ylamine With N-Ac-Leu In methanol Stage #2: 3-acetylaminophthalic anhydride With sodium hydroxide In N,N-dimethyl acetamide |
3-acetamidophthalimide
Apremilast
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; for 4h; | 70% |
3-acetamidophthalimide
(R)-3-ethoxy-4-methoxy-α-[(methylsulfonyl)methyl]benzyl alcohol
A
Apremilast
B
R-Apremilast
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran; toluene at -5 - 20℃; for 7h; Mitsunobu Displacement; Inert atmosphere; | A 65% B n/a |
With triphenylphosphine; diethylazodicarboxylate In dichloromethane; toluene at 20℃; Cooling with ice; | A 22% B n/a |
3-acetamidophthalimide
(R)-3-ethoxy-4-methoxy-α-[(methylsulfonyl)methyl]benzyl alcohol
Apremilast
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 20℃; for 15h; Solvent; Inert atmosphere; | 62% |
Stage #1: 3-acetamidophthalimide With triphenylphosphine In dichloromethane at 20℃; for 0.25h; Stage #2: (R)-3-ethoxy-4-methoxy-α-[(methylsulfonyl)methyl]benzyl alcohol With diethylazodicarboxylate In dichloromethane; toluene at 20℃; Cooling with ice; | 22% |
1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethen-1-amine
Apremilast
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; hydrogen; (R)-(-)-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethyldi-tert-butylphosphine / 2,2,2-trifluoroethanol / 18 h / 50 °C / 4654.46 Torr / Inert atmosphere 2: acetic acid / Reflux View Scheme | |
Multi-step reaction with 3 steps 1: sodium cyanoborohydride; citric acid / methanol / 1 h / 5 °C 2: acetic acid / water / 3 h / 20 - 97 °C 3: N,N-dimethyl-formamide / 8 h / 20 - 95 °C View Scheme | |
Multi-step reaction with 4 steps 1: sodium cyanoborohydride; citric acid / methanol / 1 h / 5 °C 2: acetic acid / water / 3 h / 20 - 97 °C 3: sodium hydroxide / water; toluene / 3 h / 20 °C 4: acetic acid / toluene / 100 - 105 °C View Scheme |
3-ethoxy-4-methoxybenzenecarbonitrile
Apremilast
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / 0 - 5 °C 1.2: 2 h / 0 - 30 °C 2.1: bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; hydrogen; (R)-(-)-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethyldi-tert-butylphosphine / 2,2,2-trifluoroethanol / 18 h / 50 °C / 4654.46 Torr / Inert atmosphere 3.1: acetic acid / Reflux View Scheme | |
Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 3 h / 0 - 10 °C / Inert atmosphere 1.2: 6 h / 0 - 20 °C 2.1: (S)-diphenylprolinol; Trimethyl borate; borane dimethyl sulphide complex / tetrahydrofuran / 8 h / 0 - 25 °C / Inert atmosphere 3.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 4 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran / 1.5 h / 0 - 5 °C 1.2: 1.5 h / 0 - 30 °C 2.1: methanol / 5.5 h / 45 °C / Reflux 3.1: acetic acid / 15 h / Reflux View Scheme |
3-aminophthalic acid
Apremilast
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 3 h / Reflux 2: acetic acid / Reflux View Scheme | |
Multi-step reaction with 2 steps 1: 3 h / Reflux 2: acetic acid / 15 h / Reflux View Scheme | |
Multi-step reaction with 2 steps 1: 3 h / Reflux 2: acetic acid / Reflux View Scheme |
3-nitrophthalic acid
Apremilast
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: palladium 10% on activated carbon; hydrogen / ethanol / 13 h / 2585.81 - 2844.39 Torr / Inert atmosphere 2: 3 h / Reflux 3: acetic acid / Reflux View Scheme | |
Multi-step reaction with 3 steps 1: palladium 10% on activated carbon; hydrogen / ethanol / 13 h / 2585.81 - 2844.39 Torr 2: 3 h / Reflux 3: acetic acid / 15 h / Reflux View Scheme | |
Multi-step reaction with 3 steps 1: palladium 10% on activated carbon; hydrogen / ethanol / 13 h / 2585.81 - 2844.39 Torr 2: 3 h / Reflux 3: acetic acid / Reflux View Scheme |
2-(3-ethoxy-4-methoxyphenyl)-1-(methylsulfonyl)eth-2-ylamine
Apremilast
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: methanol / 1 h / Reflux 2: acetic acid / Reflux View Scheme | |
Multi-step reaction with 2 steps 1.1: methanol / 1 h / Inert atmosphere; Reflux 2.1: sodium hydroxide / dichloromethane / 2 h / 0 - 5 °C 2.2: 3.33 h / 45 °C / Reflux View Scheme | |
Multi-step reaction with 3 steps 1: methanol / 1 h / Inert atmosphere; Reflux 2: sodium hydroxide / dichloromethane / 2 h / 0 - 5 °C 3: acetic acid; perchloric acid / 2.5 h / 85 °C / Reflux View Scheme |
1-Bromo-3-ethoxy-4-methoxybenzene
Apremilast
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: magnesium; iodine / tetrahydrofuran / 3.83 h / 45 - 60 °C 1.2: 3.67 h / -5 - 0 °C 1.3: Raney nickel / 3 h / 20 - 25 °C / 760.05 - 1520.1 Torr / Autoclave 2.1: methanol / 1 h / Inert atmosphere; Reflux 3.1: sodium hydroxide / dichloromethane / 2 h / 0 - 5 °C 3.2: 3.33 h / 45 °C / Reflux View Scheme | |
Multi-step reaction with 4 steps 1.1: magnesium; iodine / tetrahydrofuran / 3.83 h / 45 - 60 °C 1.2: 3.67 h / -5 - 0 °C 1.3: Raney nickel / 3 h / 20 - 25 °C / 760.05 - 1520.1 Torr / Autoclave 2.1: methanol / 1 h / Inert atmosphere; Reflux 3.1: sodium hydroxide / dichloromethane / 2 h / 0 - 5 °C 4.1: acetic acid; perchloric acid / 2.5 h / 85 °C / Reflux View Scheme | |
Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 1.2: 16 h / -78 - 20 °C / Inert atmosphere 2.1: triethylamine; chlorobis(ethylene)rhodium(I) dimer; (1S,4S)-2,5-diphenylbicyclo[2.2.2]octa-2,5-diene / methanol / 2 h / 60 °C / Inert atmosphere 3.1: 3 h / 70 °C / Inert atmosphere View Scheme |
Apremilast
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: ethanol / 15 h / Reflux 2.1: ammonium formate; palladium on activated charcoal / methanol; water / 15 h / Reflux 3.1: methanol / 4 h / 25 °C / Reflux 4.1: acetic acid / 15 h / Reflux 4.2: 3.25 h / 25 °C / Reflux View Scheme | |
Multi-step reaction with 5 steps 1.1: ethanol / 3 h / Reflux 2.1: D-glucose / water / 48 h / 30 °C / Enzymatic reaction 3.1: tributylphosphine; diethylazodicarboxylate; hydrogen azide / toluene; tetrahydrofuran / 22 h / -70 - 20 °C / Inert atmosphere 4.1: triphenylphosphine / water; tetrahydrofuran / Inert atmosphere; Reflux; Sealed tube 4.2: Reflux 4.3: 1 h / 80 °C / Sealed tube 5.1: acetic acid / Reflux View Scheme |
1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethan-1-one
Apremilast
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: ammonium formate; palladium on activated charcoal / methanol; water / 15 h / Reflux 2.1: methanol / 4 h / 25 °C / Reflux 3.1: acetic acid / 15 h / Reflux 3.2: 3.25 h / 25 °C / Reflux View Scheme | |
Multi-step reaction with 4 steps 1.1: D-glucose / water / 48 h / 30 °C / Enzymatic reaction 2.1: tributylphosphine; diethylazodicarboxylate; hydrogen azide / toluene; tetrahydrofuran / 22 h / -70 - 20 °C / Inert atmosphere 3.1: triphenylphosphine / water; tetrahydrofuran / Inert atmosphere; Reflux; Sealed tube 3.2: Reflux 3.3: 1 h / 80 °C / Sealed tube 4.1: acetic acid / Reflux View Scheme |
3-aminophthalic acid hydrochloride
Apremilast
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: water / 15 h / 100 °C 2.1: acetic acid / 15 h / Reflux 2.2: 3.25 h / 25 °C / Reflux View Scheme | |
Multi-step reaction with 2 steps 1.1: 2 h / 110 °C 2.1: acetonitrile / 80 - 85 °C 2.2: 60 - 65 °C View Scheme | |
Multi-step reaction with 2 steps 1: 2 h / 110 °C 2: acetonitrile / 3 h / Reflux View Scheme |
3-hydroxy-4-methoxyacetophenone
Apremilast
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 25 °C 2.1: 1,3-dichloro-5,5-dimethylhydantoin; toluene-4-sulfonic acid / methanol / 15 h / 5 - 25 °C 3.1: ethanol / 15 h / Reflux 4.1: ammonium formate; palladium on activated charcoal / methanol; water / 15 h / Reflux 5.1: methanol / 4 h / 25 °C / Reflux 6.1: acetic acid / 15 h / Reflux 6.2: 3.25 h / 25 °C / Reflux View Scheme | |
Multi-step reaction with 6 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 30 - 35 °C 2.1: toluene-4-sulfonic acid; N-Bromosuccinimide / ethyl acetate / 16 h / 25 - 30 °C 3.1: methanol; water / 0.01 h / 35 - 40 °C 4.1: titanium(IV) isopropylate; (R)-2-methylpropane-2-sulfinamide / ethyl acetate / 65 h / 45 °C 4.2: 0.75 h / 0 - 20 °C 4.3: 1 h / 20 °C 5.1: sodium hydroxide / water 6.1: acetic acid / acetonitrile / 12 h / Reflux 6.2: 7 h / 20 °C / Cooling View Scheme | |
Multi-step reaction with 6 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 30 - 35 °C 2.1: toluene-4-sulfonic acid; N-Bromosuccinimide / ethyl acetate / 16 h / 25 - 30 °C 3.1: methanol; water / 0.01 h / 35 - 40 °C 4.1: titanium(IV) isopropylate; (R)-2-methylpropane-2-sulfinamide / ethyl acetate / 65 h / 45 °C 4.2: 0.75 h / 0 - 20 °C 4.3: 1 h / 20 °C 5.1: sodium hydroxide / water 6.1: acetic acid / acetonitrile / 12 h / Reflux 6.2: 7 h / 20 °C / Cooling View Scheme | |
Multi-step reaction with 7 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 30 - 35 °C 2.1: toluene-4-sulfonic acid; N-Bromosuccinimide / ethyl acetate / 16 h / 25 - 30 °C 3.1: methanol; water / 0.01 h / 35 - 40 °C 4.1: titanium(IV) isopropylate; (R)-2-methylpropane-2-sulfinamide / ethyl acetate / 65 h / 45 °C 4.2: 0.75 h / 0 - 20 °C 4.3: 1 h / 20 °C 5.1: sodium hydroxide / water 6.1: acetic acid / acetonitrile / 12 h / Reflux 7.1: acetic acid / acetonitrile / 20 °C 7.2: 7 h / 20 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 30 - 35 °C 2.1: toluene-4-sulfonic acid; N-Bromosuccinimide / ethyl acetate / 16 h / 25 - 30 °C 3.1: methanol; water / 0.01 h / 35 - 40 °C 4.1: titanium(IV) isopropylate; (R)-2-methylpropane-2-sulfinamide / ethyl acetate / 65 h / 45 °C 4.2: 0.75 h / 0 - 20 °C 4.3: 1 h / 20 °C 5.1: sodium hydroxide / water 6.1: acetic acid / acetonitrile / 12 h / Reflux 7.1: acetic acid / acetonitrile / 20 °C 7.2: 7 h / 20 °C View Scheme |
3-ethoxy-4-methoxy-acetophenone
Apremilast
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: 1,3-dichloro-5,5-dimethylhydantoin; toluene-4-sulfonic acid / methanol / 15 h / 5 - 25 °C 2.1: ethanol / 15 h / Reflux 3.1: ammonium formate; palladium on activated charcoal / methanol; water / 15 h / Reflux 4.1: methanol / 4 h / 25 °C / Reflux 5.1: acetic acid / 15 h / Reflux 5.2: 3.25 h / 25 °C / Reflux View Scheme | |
Multi-step reaction with 6 steps 1.1: N-chloro-succinimide; toluene-4-sulfonic acid / acetonitrile / 40 °C 2.1: ethanol / 3 h / Reflux 3.1: D-glucose / water / 48 h / 30 °C / Enzymatic reaction 4.1: tributylphosphine; diethylazodicarboxylate; hydrogen azide / toluene; tetrahydrofuran / 22 h / -70 - 20 °C / Inert atmosphere 5.1: triphenylphosphine / water; tetrahydrofuran / Inert atmosphere; Reflux; Sealed tube 5.2: Reflux 5.3: 1 h / 80 °C / Sealed tube 6.1: acetic acid / Reflux View Scheme | |
Multi-step reaction with 5 steps 1.1: toluene-4-sulfonic acid; N-Bromosuccinimide / ethyl acetate / 16 h / 25 - 30 °C 2.1: methanol; water / 0.01 h / 35 - 40 °C 3.1: titanium(IV) isopropylate; (R)-2-methylpropane-2-sulfinamide / ethyl acetate / 65 h / 45 °C 3.2: 0.75 h / 0 - 20 °C 3.3: 1 h / 20 °C 4.1: sodium hydroxide / water 5.1: acetic acid / acetonitrile / 12 h / Reflux 5.2: 7 h / 20 °C / Cooling View Scheme | |
Multi-step reaction with 6 steps 1.1: toluene-4-sulfonic acid; N-Bromosuccinimide / ethyl acetate / 16 h / 25 - 30 °C 2.1: methanol; water / 0.01 h / 35 - 40 °C 3.1: titanium(IV) isopropylate; (R)-2-methylpropane-2-sulfinamide / ethyl acetate / 65 h / 45 °C 3.2: 0.75 h / 0 - 20 °C 3.3: 1 h / 20 °C 4.1: sodium hydroxide / water 5.1: acetic acid / acetonitrile / 12 h / Reflux 6.1: acetic acid / acetonitrile / 20 °C 6.2: 7 h / 20 °C View Scheme |
(S)-2-[1 (3-ethoxy-4-methoxyphenyl)]-1-methanesulfonyl-2-ethylamine
3-acetylaminophthalic acid
Apremilast
Conditions | Yield |
---|---|
With triethanolamine; benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 1h; | 4.2 g |
isovanillin
Apremilast
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: sodium formate; hydroxylamine hydrochloride / formic acid / 5 h / 85 °C 2.1: potassium carbonate / N,N-dimethyl-formamide / 8 h / 100 °C 3.1: n-butyllithium / tetrahydrofuran; hexane / 3 h / 0 - 10 °C / Inert atmosphere 3.2: 6 h / 0 - 20 °C 4.1: (S)-diphenylprolinol; Trimethyl borate; borane dimethyl sulphide complex / tetrahydrofuran / 8 h / 0 - 25 °C / Inert atmosphere 5.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 4 h / 0 - 20 °C View Scheme |
Conditions | Yield |
---|---|
With pentamethylcyclopentadienyl(benzene)cobalt(III) hexafluorophosphate; potassium carbonate; silver carbonate In 2-methyltetrahydrofuran at 100℃; for 16h; Inert atmosphere; Sealed tube; | 23% |
Conditions | Yield |
---|---|
Stage #1: Apremilast With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile for 3h; Reflux; Stage #2: octa-acetyl lactulose With trimethylsilyl trifluoromethanesulfonate at 20℃; for 14h; | 16.7% |
Stage #1: Apremilast With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile for 3h; Reflux; Stage #2: octa-acetyl lactulose With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 20℃; for 14.0833h; | 16.7% |
Apremilast
(S)-N-{2-[1-(3-hydroxy-4-methoxy-phenyl)-2-methanesulfonyl-ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}-acetamide
Conditions | Yield |
---|---|
With aluminum (III) chloride In dichloromethane at 20℃; for 1h; |
Apremilast
(S)-N-(2-(1-(3-ethoxy-4-hydroxyphenyl)-2-(methylsulfonyl)ethyl)-1,3-dioxoisoindolin-4-yl)acetamide
Conditions | Yield |
---|---|
With trimethylsilyl iodide In dichloromethane at 20℃; for 24h; |
Apremilast
(S)-N-{2-[1-(3,4-dihydroxy-phenyl)-2-methanesulfonyl-ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}-acetamide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: trimethylsilyl iodide / dichloromethane / 24 h / 20 °C 2: aluminum (III) chloride / dichloromethane / 1 h / 20 °C View Scheme |
Apremilast
(2S,3R,4S,5S,6S)-2-(4-((S)-1-(4-acetamido-1,3-dioxoisoindolin-2-yl)-2-(methylsulfonyl)ethyl)-2-ethoxyphenoxy)-6-((benzyloxy)carbonyl)tetrahydro-2H-pyran-3,4,5-triyltriacetate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: trimethylsilyl iodide / dichloromethane / 24 h / 20 °C 2: boron trifluoride diethyl etherate / dichloromethane / 6 h / -18 - 25 °C / Molecular sieve View Scheme |
Apremilast
C33H36N2O16S
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: trimethylsilyl iodide / dichloromethane / 24 h / 20 °C 2: boron trifluoride diethyl etherate / dichloromethane / 6 h / -18 - 25 °C / Molecular sieve 3: hydrogen / palladium 10% on activated carbon / ethyl acetate / 12 h / 1551.49 - 2068.65 Torr View Scheme |
Apremilast
(S)-N-{2-[1-(3-ethoxy-4-glucopyranuroxy-phenyl)-2-methanesulfonyl-ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}-acetamide
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: trimethylsilyl iodide / dichloromethane / 24 h / 20 °C 2: boron trifluoride diethyl etherate / dichloromethane / 6 h / -18 - 25 °C / Molecular sieve 3: hydrogen / palladium 10% on activated carbon / ethyl acetate / 12 h / 1551.49 - 2068.65 Torr 4: sodium carbonate / methanol / 2 h / 60 °C View Scheme |
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