Analysis tests Standard Results Appearance White or off-white crystalline powder Conforms Identification
Cas:99011-02-6
Min.Order:10 Gram
FOB Price: $1.5 / 3.0
Type:Manufacturers
inquiryImiquimod[CAS:99011-02-6] Name Imiquimod Synonyms 4-Amino- 1-isobutyl-1H-imidazo[4,5-c]quinoline; 1-(2-Methylpropyl)-1H-imidazo[4,5-C]quinolin-4-amine
DayangChem exported this product to many countries and regions at best price. If you are looking for the material's manufacturer or supplier in China, DayangChem is your best choice. Pls contact with us freely for getting detailed product spe
hebei 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
Cas:99011-02-6
Min.Order:1 Metric Ton
FOB Price: $1.0 / 3.0
Type:Manufacturers
inquiryUnique advantages of Imiquimod CAS 99011-02-6 Guaranteed purity High quality & competitive price Quality control Fast feedback Prompt shipment Appearance:White crystalline powder Storage:Normal temperature preservation Package:1kg/foi
Cas:99011-02-6
Min.Order:1 Kilogram
Negotiable
Type:Trading Company
inquiryJinlan 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
Xi’an Quanao Biotech Co., Ltd. with 18 years experience in plant extract filed. Product grade: Medicine, Health care product, Cosmetics, Food, Beverage, Feed. Hot selling market: Europe, North America, South America, Middle East, Asia Pacifi
Cas:99011-02-6
Min.Order:1 Kilogram
FOB Price: $2599.0 / 2699.0
Type:Manufacturers
inquiryThe above product is Ality Chemical's strong item with best price, good quality and fast supply. Ality Chemical has been focusing on the research and production of this field for over 14 years. At the same time, we are always committed to providi
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
Cas:99011-02-6
Min.Order:1 Gram
FOB Price: $0.1
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
Imiquimod Basic information Product Name: Imiquimod Synonyms: R-837;S-26308;1-(2-METHYLPROPYL)-1H-IMIDAZO[4,5-C]QUINOLIN-4-AMINE;4-amino- 1-isobutyl-1h-imidazo[4,5-c]quinoline;ALDARA;IMI
Our advantages: 1. All inquiries will be replied within 12 hours. 2. Dedication to quality, supply & service. 3. Strictly on selecting raw materials. 4. Reasonable & competitive price, fast lead time. 5. Sample is available for your eva
WITH 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
Cas:99011-02-6
Min.Order:1 Kilogram
FOB Price: $139.0 / 210.0
Type:Trading Company
inquiryOur Advantage: high quality with competitive price High quality standard: BP/USP/EP Enterprise standard All purity customized Fast and safe delivery We have reliable forwarder who can help us deliver our goods more fast and safe. We
Cas:99011-02-6
Min.Order:10 Kilogram
Negotiable
Type:Trading Company
inquiryProduct Name: Imiquimod CAS NO.:99011-02-6 Appearance:yellowish crystalline powder Molecular Formula:C14H16N4 Molecular Weight:240.31 Assay:99% Appearance:White powder Storage:Store in cool and dry place, away from sun light. Package:25kg
Cas:99011-02-6
Min.Order:5 Metric Ton
FOB Price: $1.0 / 2.0
Type:Other
inquiryAppearance:White powder Storage:Keep in dark place,Inert atmosphere,Store in freezer, under -20°C Package:25kg/drum Application:It can be used for anti-genital warts and as immunomodulators Transportation:Express/Sea/Air Port:any port in china
Cas:99011-02-6
Min.Order:1 Kilogram
FOB Price: $1.0
Type:Lab/Research institutions
inquiry1,In No Less five years exporting experience. 2.Lower Price with higher quality 3,Free sample 4,We are sincerely responsible for the "product quality" and "After Service" Onchem (China) Co.,Ltd is Sp
Cas:99011-02-6
Min.Order:10 Gram
Negotiable
Type:Lab/Research institutions
inquiryWe are the manufacturers and suppliers of API in China, and warehouse in Germany and USA of California, which can quickly and safely deliver to your address 1.High quality and competitive price. 2.Free sample for your evaluation. 3.Promptly delivery
Cas:99011-02-6
Min.Order:10 Gram
FOB Price: $3.5
Type:Trading Company
inquiry★.Best quality according to requirement ★.Competitive price in China market ★.Mature Technical support ★.Professional logistic support ★.Shortest delivery time . Appearance:Refer to COA Storage:Store in dry, cool and ventilated place Package:Acc
Our company has been in existence for 10 years since its establishment. We have our own unique team. The company integrates independent research and development, production and sales. We have established famous brands at home and abroad. At present
Imiquimod CAS:99011-02-6 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production and trade of chemical intermediates, specializing in high quality organic intermediates,
Cas:99011-02-6
Min.Order:1 Gram
Negotiable
Type:Lab/Research institutions
inquiryHello, dear friend! I'm Hansen and Allen from China. Welcome to my lookchem mall! The following is a brief introduction of our company's products and services. If you are interested in our products, please contact us by emai
Hebei Mojin Biotechnology Co., Ltd, Our company is a professional chemical raw materials and chemical reagents research and development production enterprises. We have several production line,So we can control the lowest price. We also have several
Cas:99011-02-6
Min.Order:25 Gram
FOB Price: $90.0 / 100.0
Type:Trading Company
inquiryHenan 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
Our Services 1. New Molecules R&D 2. Own test center HPLC NMR GC LC-MS 3. API and Intermediates from China reputed manufacturers 4. Documents support COA MOA MSDS DMF open part Our advantages 1. Government awarded company. Top 100 enter
Our company provides one-stop services of research - development - production for a variety of special prouducts. Not only do we make effective use of our strong technological strength, but also establish of cooperative relations with several well-
Cas:99011-02-6
Min.Order:1 Gram
Negotiable
Type:Lab/Research institutions
inquiryJ&H CHEM 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. J&H CHEM has some Manufacturing base in Jia
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:99011-02-6
Min.Order:10 Gram
FOB Price: $100.0
Type:Lab/Research institutions
inquiryWe are one of a few suppliers that can offer custom synthesis service of this product We are specialized in custom synthesis, chemical/pharmaceutical/ pesticides outsourcing and contract research. We are committed to prov
Cas:99011-02-6
Min.Order:100 Gram
FOB Price: $100.0 / 2000.0
Type:Lab/Research institutions
inquirySuperior quality Appearance:White to off white crystalline powder Storage:Stored in cool, dry and ventilation place; Away from fire and heat Package:1kg/bag, 1kg/drum or 25kg/drum or as per your request. Application:An immune response modifier. It
4-Hydrazino-1-(2-methylpropyl)-1H-imidazo [4,5-c]quinoline
imiqimod
Conditions | Yield |
---|---|
With hydrogenchloride; sodium formate; palladium 10% on activated carbon In water for 84h; Product distribution / selectivity; Heating / reflux; | 98% |
Stage #1: 4-Hydrazino-1-(2-methylpropyl)-1H-imidazo [4,5-c]quinoline With hydrogenchloride; sodium formate; palladium 10% on activated carbon In water for 84h; Heating / reflux; Stage #2: With hydrogenchloride In water at 20℃; Stage #3: With ammonia In water at 20℃; Product distribution / selectivity; | 98% |
4-chloro-1H-imidazo[4,5-c]-quinoline
imiqimod
Conditions | Yield |
---|---|
Stage #1: formamide With potassium tert-butylate In dimethyl sulfoxide for 0.5h; Stage #2: 4-chloro-1H-imidazo[4,5-c]-quinoline In dimethyl sulfoxide at 105℃; for 2h; Stage #3: With hydrogenchloride In water; dimethyl sulfoxide pH=8; Product distribution / selectivity; | 98% |
imiqimod
Conditions | Yield |
---|---|
With ethylenediamine In water at 70 - 95℃; for 4h; | 91.8% |
Stage #1: N-(1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)-phthalimide With hydrazine In water at 70℃; Stage #2: With 2,4,4-trimethylpentan-1-ol In water at 94 - 95℃; for 5h; Stage #3: In methanol; water at 60℃; for 0.25h; Heating / reflux; | 63.3% |
imiqimod
Conditions | Yield |
---|---|
With ammonia; water In methanol Product distribution / selectivity; | 90% |
5-(2-aminophenyl)-1-(2-methylpropyl)-1H-imidazole-4-carbonitrile
imiqimod
Conditions | Yield |
---|---|
With sodium amide In toluene at 20 - 100℃; for 2h; | 90% |
imiqimod
Conditions | Yield |
---|---|
Stage #1: 4-amino-1-isobutyl-1H-imidazo-[4,5-c]-quinoline maleate In methanol; water at 75℃; for 0.5h; Stage #2: With ammonia In water | 89.7% |
With ammonia; water In methanol Product distribution / selectivity; | 89.7% |
imiqimod
Conditions | Yield |
---|---|
With ammonia; water In methanol Product distribution / selectivity; | 88% |
4-iodo-1-isobutyl-1H-imidazo-[4,5-c]-quinoline
imiqimod
Conditions | Yield |
---|---|
With ammonia In methanol at 150 - 155℃; Autoclave (ca. 20 kg pressure); | 86% |
With ammonia In methanol at 150 - 155℃; under 14711.4 Torr; Product distribution / selectivity; Autoclave; | 86% |
4-Chloro-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline
imiqimod
Conditions | Yield |
---|---|
With ammonia In dimethyl sulfoxide at 20 - 150℃; under 1875.19 - 3750.38 Torr; for 6 - 12h; Product distribution / selectivity; | 85.7% |
With ammonia at 150℃; for 7h; | 82% |
With ammonia; formamide at 145℃; for 20 - 25h; Product distribution / selectivity; | 78% |
imiqimod
Conditions | Yield |
---|---|
Stage #1: imiquimod hydrochloride With sodium hydrogensulfide; pyrographite In water at 85 - 90℃; for 0.333333h; Stage #2: With ammonium hydroxide In water at 20 - 80℃; Purification / work up; | 80.5% |
With sodium hydroxide In water at 20℃; for 0.5h; Product distribution / selectivity; |
1-Isobutyl-2-methylsulfanyl-1H-imidazo[4,5-c]quinolin-4-ylamine
imiqimod
Conditions | Yield |
---|---|
With sodium bis(2-methoxyethoxy)aluminium dihydride In toluene for 0.5h; Heating; | 80% |
1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline 5N-oxide
imiqimod
Conditions | Yield |
---|---|
With ammonia; chloroformic acid ethyl ester In dichloromethane; water at 0 - 20℃; for 1h; Cooling with methanol-ice bath; | 76% |
With ammonium hydroxide; p-toluenesulfonyl chloride In dichloromethane at 20℃; for 0.25h; | 71% |
Multi-step reaction with 2 steps 1: 49 percent / POCl3 / CH2Cl2 / 0.25 h / Heating 2: 82 percent / methanolic NH3 / 7 h / 150 °C View Scheme | |
Multi-step reaction with 2 steps 1: CH2Cl2 / 0.25 h / Heating 2: NaOMe / methanol / 2 h / Heating View Scheme |
imiqimod
Conditions | Yield |
---|---|
Stage #1: formamide With potassium tert-butylate In ISOPROPYLAMIDE for 0.5h; Stage #2: 4-bromo-1H-imidazo[4,5-c]quinoline In ISOPROPYLAMIDE at 140℃; for 2h; Product distribution / selectivity; | 75.4% |
imiqimod
Conditions | Yield |
---|---|
With hydrogenchloride; zinc In ethanol; water at 20℃; for 1h; Product distribution / selectivity; | 70% |
Stage #1: N-(1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)-O-methyl-hydroxylamine With hydrogenchloride; zinc In ethanol; water at 20℃; for 1h; Stage #2: With sodium hydroxide In ethanol; water for 0.5h; Product distribution / selectivity; | 70% |
1-isobutyl-1H-imidazo[4,5-c]quinolin-4-guanidine
imiqimod
Conditions | Yield |
---|---|
Stage #1: 1-isobutyl-1H-imidazo[4,5-c]quinolin-4-guanidine With sulfuric acid; water In dimethyl sulfoxide at 140℃; for 20h; Stage #2: With sodium hydroxide; water In dimethyl sulfoxide at 20 - 60℃; for 2h; pH=10 - 11; Product distribution / selectivity; | 70% |
Stage #1: 1-isobutyl-1H-imidazo[4,5-c]quinolin-4-guanidine In dimethyl sulfoxide at 140 - 150℃; for 9h; Stage #2: With sodium hydroxide; water In dimethyl sulfoxide at 20 - 60℃; for 2h; pH=10 - 11; Product distribution / selectivity; |
4-chloro-1H-imidazo[4,5-c]-quinoline
B
imiqimod
Conditions | Yield |
---|---|
Stage #1: formamide With potassium tert-butylate In ISOPROPYLAMIDE for 0.5h; Stage #2: 4-chloro-1H-imidazo[4,5-c]-quinoline In ISOPROPYLAMIDE at 120℃; for 1h; Product distribution / selectivity; | A 54% B 39% |
N-benzoyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine
imiqimod
Conditions | Yield |
---|---|
With sodium methylate In methanol for 2h; Heating; |
1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline
imiqimod
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: peracetic acid / ethanol / 2.5 h / 60 °C 2: 49 percent / POCl3 / CH2Cl2 / 0.25 h / Heating 3: 82 percent / methanolic NH3 / 7 h / 150 °C View Scheme | |
Multi-step reaction with 2 steps 1: peracetic acid / ethanol / 2.5 h / 60 °C 2: 71 percent / aq. NH3; tosyl chloride / CH2Cl2 / 0.25 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: peracetic acid / ethanol / 2.5 h / 60 °C 2: CH2Cl2 / 0.25 h / Heating 3: NaOMe / methanol / 2 h / Heating View Scheme |
3-Amino-4-(2-methylpropylamino)-quinoline
imiqimod
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 1 h / Heating 2: peracetic acid / ethanol / 2.5 h / 60 °C 3: 49 percent / POCl3 / CH2Cl2 / 0.25 h / Heating 4: 82 percent / methanolic NH3 / 7 h / 150 °C View Scheme | |
Multi-step reaction with 3 steps 1: 1 h / Heating 2: peracetic acid / ethanol / 2.5 h / 60 °C 3: 71 percent / aq. NH3; tosyl chloride / CH2Cl2 / 0.25 h / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1: 1 h / Heating 2: peracetic acid / ethanol / 2.5 h / 60 °C 3: CH2Cl2 / 0.25 h / Heating 4: NaOMe / methanol / 2 h / Heating View Scheme |
N-(2-methylpropyl)-3-nitro-4-quinolinamine
imiqimod
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: H2; MgSO4 / Pt/C / ethyl acetate / 2740.88 Torr 2: 1 h / Heating 3: peracetic acid / ethanol / 2.5 h / 60 °C 4: 49 percent / POCl3 / CH2Cl2 / 0.25 h / Heating 5: 82 percent / methanolic NH3 / 7 h / 150 °C View Scheme | |
Multi-step reaction with 4 steps 1: H2; MgSO4 / Pt/C / ethyl acetate / 2740.88 Torr 2: 1 h / Heating 3: peracetic acid / ethanol / 2.5 h / 60 °C 4: 71 percent / aq. NH3; tosyl chloride / CH2Cl2 / 0.25 h / 20 °C View Scheme | |
Multi-step reaction with 5 steps 1: H2; MgSO4 / Pt/C / ethyl acetate / 2740.88 Torr 2: 1 h / Heating 3: peracetic acid / ethanol / 2.5 h / 60 °C 4: CH2Cl2 / 0.25 h / Heating 5: NaOMe / methanol / 2 h / Heating View Scheme |
2-chloro-N4-(2-methylpropyl)quinoline-3,4-diamine
imiqimod
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 61 percent / toluene / 1.5 h / Heating 2: 82 percent / methanolic NH3 / 7 h / 150 °C View Scheme |
2-chloro-N4-(2-methylpropyl)-3-nitroquinoline-4-amine
imiqimod
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: H2; MgSO4 / Pt/C / ethyl acetate / 2585.74 Torr 2: 61 percent / toluene / 1.5 h / Heating 3: 82 percent / methanolic NH3 / 7 h / 150 °C View Scheme |
quinolin-4-ol
imiqimod
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: 81 percent / aq. HNO3 / propionic acid / 0.25 h / 125 °C 2: SOCl2; DMF / CH2Cl2 / 3 h / Heating 3: Et3N / CH2Cl2 / 0.25 h / Heating 4: H2; MgSO4 / Pt/C / ethyl acetate / 2740.88 Torr 5: 1 h / Heating 6: peracetic acid / ethanol / 2.5 h / 60 °C 7: 49 percent / POCl3 / CH2Cl2 / 0.25 h / Heating 8: 82 percent / methanolic NH3 / 7 h / 150 °C View Scheme | |
Multi-step reaction with 7 steps 1: 81 percent / aq. HNO3 / propionic acid / 0.25 h / 125 °C 2: SOCl2; DMF / CH2Cl2 / 3 h / Heating 3: Et3N / CH2Cl2 / 0.25 h / Heating 4: H2; MgSO4 / Pt/C / ethyl acetate / 2740.88 Torr 5: 1 h / Heating 6: peracetic acid / ethanol / 2.5 h / 60 °C 7: 71 percent / aq. NH3; tosyl chloride / CH2Cl2 / 0.25 h / 20 °C View Scheme | |
Multi-step reaction with 8 steps 1: 81 percent / aq. HNO3 / propionic acid / 0.25 h / 125 °C 2: SOCl2; DMF / CH2Cl2 / 3 h / Heating 3: Et3N / CH2Cl2 / 0.25 h / Heating 4: H2; MgSO4 / Pt/C / ethyl acetate / 2740.88 Torr 5: 1 h / Heating 6: peracetic acid / ethanol / 2.5 h / 60 °C 7: CH2Cl2 / 0.25 h / Heating 8: NaOMe / methanol / 2 h / Heating View Scheme |
4-hydroxy-3-nitro-1,2-dihydroquinolin-2-one
imiqimod
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: POCl3; Et3N / toluene / 4 h / 80 - 90 °C 2: 17.8 g / Et3N / CH2Cl2 / 0.5 h / Heating 3: H2; MgSO4 / Pt/C / ethyl acetate / 2585.74 Torr 4: 61 percent / toluene / 1.5 h / Heating 5: 82 percent / methanolic NH3 / 7 h / 150 °C View Scheme |
3-nitro-quinolin-4-ol
imiqimod
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: SOCl2; DMF / CH2Cl2 / 3 h / Heating 2: Et3N / CH2Cl2 / 0.25 h / Heating 3: H2; MgSO4 / Pt/C / ethyl acetate / 2740.88 Torr 4: 1 h / Heating 5: peracetic acid / ethanol / 2.5 h / 60 °C 6: 49 percent / POCl3 / CH2Cl2 / 0.25 h / Heating 7: 82 percent / methanolic NH3 / 7 h / 150 °C View Scheme | |
Multi-step reaction with 6 steps 1: SOCl2; DMF / CH2Cl2 / 3 h / Heating 2: Et3N / CH2Cl2 / 0.25 h / Heating 3: H2; MgSO4 / Pt/C / ethyl acetate / 2740.88 Torr 4: 1 h / Heating 5: peracetic acid / ethanol / 2.5 h / 60 °C 6: 71 percent / aq. NH3; tosyl chloride / CH2Cl2 / 0.25 h / 20 °C View Scheme | |
Multi-step reaction with 7 steps 1: SOCl2; DMF / CH2Cl2 / 3 h / Heating 2: Et3N / CH2Cl2 / 0.25 h / Heating 3: H2; MgSO4 / Pt/C / ethyl acetate / 2740.88 Torr 4: 1 h / Heating 5: peracetic acid / ethanol / 2.5 h / 60 °C 6: CH2Cl2 / 0.25 h / Heating 7: NaOMe / methanol / 2 h / Heating View Scheme |
4-chloro-3-nitroquinoline
imiqimod
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: Et3N / CH2Cl2 / 0.25 h / Heating 2: H2; MgSO4 / Pt/C / ethyl acetate / 2740.88 Torr 3: 1 h / Heating 4: peracetic acid / ethanol / 2.5 h / 60 °C 5: 49 percent / POCl3 / CH2Cl2 / 0.25 h / Heating 6: 82 percent / methanolic NH3 / 7 h / 150 °C View Scheme | |
Multi-step reaction with 5 steps 1: Et3N / CH2Cl2 / 0.25 h / Heating 2: H2; MgSO4 / Pt/C / ethyl acetate / 2740.88 Torr 3: 1 h / Heating 4: peracetic acid / ethanol / 2.5 h / 60 °C 5: 71 percent / aq. NH3; tosyl chloride / CH2Cl2 / 0.25 h / 20 °C View Scheme | |
Multi-step reaction with 6 steps 1: Et3N / CH2Cl2 / 0.25 h / Heating 2: H2; MgSO4 / Pt/C / ethyl acetate / 2740.88 Torr 3: 1 h / Heating 4: peracetic acid / ethanol / 2.5 h / 60 °C 5: CH2Cl2 / 0.25 h / Heating 6: NaOMe / methanol / 2 h / Heating View Scheme |
2,4-dichloro-3-nitroquinoline
imiqimod
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 17.8 g / Et3N / CH2Cl2 / 0.5 h / Heating 2: H2; MgSO4 / Pt/C / ethyl acetate / 2585.74 Torr 3: 61 percent / toluene / 1.5 h / Heating 4: 82 percent / methanolic NH3 / 7 h / 150 °C View Scheme |
2-bromobenzoic acid methyl ester
imiqimod
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: PdCl2(PPh3)2, K2CO3, Et4N(1+)Cl(1-) / dimethylformamide / 2 h / 110 °C 2: 10percent aq. NaOH / dioxane / 12 h / Heating 3: Et3N, DPPA / benzene / 1 h / 50 °C 4: 1,2-dichloro-benzene / 1 h / Heating 5: 88 percent / POCl3 / 1 h / Heating 6: 93 percent / 28percent NH4OH / methanol / 48 h / 150 °C 7: 80 percent / sodium bis(2-methoxyethoxy)aluminium hydride / toluene / 0.5 h / Heating View Scheme |
1-isobuty-1H-limidazole
imiqimod
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, RT, 12 h 2: 83 percent / NBS / CCl4 / 1 h / Ambient temperature 3: 98 percent / Pd(PPh3)4, aq. Na2CO3 / toluene; ethanol / 4 h / 110 °C 4: 98 percent / NBS / CCl4 / 1 h 5: 1.) n-BuLi / 1.) Et2O, hexane, -78 deg C, 1 h, 2.) Et2O, hexane, RT, 12 h 6: 46 percent / Et3N, PPh3, CCl4 / acetonitrile / 1.) RT, 1 h, 2.) reflux, 3 h 7: 62 percent / 1,2-dichloro-benzene / 8 h / Heating 8: 41 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene / 4 h / Heating 9: 93 percent / 28percent NH4OH / methanol / 48 h / 150 °C 10: 80 percent / sodium bis(2-methoxyethoxy)aluminium hydride / toluene / 0.5 h / Heating View Scheme |
Conditions | Yield |
---|---|
In methanol; water at 74℃; Heating / reflux; | 91% |
imiqimod
Conditions | Yield |
---|---|
With maleic acid In methanol; water at 74℃; for 0.5h; | 91% |
Conditions | Yield |
---|---|
In water; N,N-dimethyl-formamide at 160℃; for 0.5h; | 90% |
(2E)-but-2-enedioic acid
imiqimod
Conditions | Yield |
---|---|
In water; N,N-dimethyl-formamide at 160℃; for 0.5h; | 89% |
N-t-butyloxycarbonyl-N-methylglycine anhydride
imiqimod
Conditions | Yield |
---|---|
With triethylamine for 8h; Reflux; | 87.5% |
With triethylamine In ethyl acetate for 2h; Reflux; | 87.5% |
imiqimod
Conditions | Yield |
---|---|
With deuterium In N,N-dimethyl acetamide under 1500.15 Torr; for 24h; Glovebox; Heating; | 80% |
imiqimod
benzyl alcohol
N-benzyl-1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine
Conditions | Yield |
---|---|
With palladium diacetate; sodium 3-(diphenylphosphanyl)benzenesulfonate In water at 140℃; for 18h; Sealed tube; | 72% |
Conditions | Yield |
---|---|
With copper(l) iodide; N,N'-dibenzylethanediamide; potassium tert-butylate In tert-butyl alcohol at 100℃; for 24h; Molecular sieve; Schlenk technique; Inert atmosphere; | 43% |
(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(2-nitro-4-((((4-nitrophenoxy)carbonyl)oxy)methyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
imiqimod
Conditions | Yield |
---|---|
Stage #1: imiqimod With N-ethyl-N,N-diisopropylamine In ethyl acetate for 0.333333h; Microwave irradiation; Stage #2: (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(2-nitro-4-((((4-nitrophenoxy)carbonyl)oxy)methyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate In ethyl acetate at 87℃; for 0.75h; Microwave irradiation; | 40% |
Stage #1: imiqimod With N-ethyl-N,N-diisopropylamine In ethyl acetate Microwave irradiation; Stage #2: (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(2-nitro-4-((((4-nitrophenoxy)carbonyl)oxy)methyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate In ethyl acetate at 87℃; for 0.75h; Microwave irradiation; | 40% |
imiqimod
Conditions | Yield |
---|---|
In tetrahydrofuran at 90℃; under 750.075 Torr; for 0.833333h; Microwave irradiation; Sealed tube; | 39% |
Conditions | Yield |
---|---|
In 1,4-dioxane at 10 - 50℃; for 6h; | 38% |
Conditions | Yield |
---|---|
With HATU In dichloromethane at 20℃; | 35% |
imiqimod
8-bromo-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine
Conditions | Yield |
---|---|
With bromine; acetic acid at 20℃; for 18h; | 26% |
Stage #1: imiqimod With bromine In acetic acid for 24h; Stage #2: With sodium carbonate In water for 18h; | |
With N-Bromosuccinimide In chloroform at 20 - 50℃; for 1.83333h; Heating / reflux; |
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