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Dayang Chem (Hangzhou) Co.,Ltd.

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

4-(2-OXO-2,3-DIHYDRO-1H-BENZO[D]IMIDAZOL-1-YL)BUTANOIC ACID

Cas:3273-68-5

Min.Order:1 Kilogram

FOB Price: $3.0

Type:Lab/Research institutions

inquiry

Henan Allgreen Chemical Co.,Ltd

Good quality Good price Promptly delivery Appearance:white powder Storage:dry dondition Package:According to the demand of customer Application:intermediate Port:shanghai

3273-68-5 1H-BENZIMIDAZOLE-1-BUTANOIC ACID, 2,3-DIHYDRO-2-OXO

Cas:3273-68-5

Min.Order:1 Kilogram

Negotiable

Type:Manufacturers

inquiry

Chemwill Asia Co., Ltd.

Our 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

2,3-Dihydro-2-oxo-1H-benzimidazole-1-butyric acid

Cas:3273-68-5

Min.Order:5 Kiloliter

FOB Price: $1.2 / 5.0

Type:Manufacturers

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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 on.

3273-68-5 1H-BENZIMIDAZOLE-1-BUTANOIC ACID, 2,3-DIHYDRO-2-OXO

Cas:3273-68-5

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Zhuozhou Wenxi import and Export Co., Ltd

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

Pharmaceutical Grade CAS 3273-68-5 with competitive price

Cas:3273-68-5

Min.Order:1 Kilogram

FOB Price: $139.0 / 210.0

Type:Trading Company

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Hebei Sankai Chemical Technology Co., Ltd

1. Product advantages ♦ High purity, all above 98.5%, no impurities after dissolution ♦ We will test each batch to ensure quality ♦ OEM and private brand services designed for free ♦ Various cap colors available ♦ W

1H-BENZIMIDAZOLE-1-BUTANOIC ACID, 2,3-DIHYDRO-2-OXO CAS:3273-68-5

Cas:3273-68-5

Min.Order:1 Kilogram

FOB Price: $38.0 / 59.0

Type:Trading Company

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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

2-Oxo-1-benzimidazolinebutyric Acid

Cas:3273-68-5

Min.Order:1 Kilogram

FOB Price: $1.0 / 10.0

Type:Trading Company

inquiry

Shanghai Upbio Tech Co.,Ltd

1.In No Less 10 years exporting experience. you can 100% received goods 2.Lower Price with higher quality 3,Free sample 4,We are sincerely responsible for the "product quality" and "After Service" Upbio is Specializ

1H-Benzimidazole-1-butanoicacid, 2,3-dihydro-2-oxo-

Cas:3273-68-5

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Shandong Hanjiang Chemical Co., Ltd.

Hello, 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

1H-Benzimidazole-1-butanoicacid, 2,3-dihydro-2-oxo-

Cas:3273-68-5

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

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

1H-Benzimidazole-1-butanoicacid, 2,3-dihydro-2-oxo-

Cas:3273-68-5

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

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

1H-BENZIMIDAZOLE-1-BUTANOIC ACID, 2,3-DIHYDRO-2-OXO

Cas:3273-68-5

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

SHANGHAI T&W PHARMACEUTICAL CO., LTD.

A substitute for perfluorooctanoic acid, mainly used as a surfactant, dispersant, additive, etc Appearance:White solid or Colorless liquid Purity:99.3 % We will ship the goods in a timely manner as required We can provide relevant documents acc

4-(2-oxo-2,3-dihydro-1H-1,3-benzodiazol-1-yl)butanoic acid

Cas:3273-68-5

Min.Order:4 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Hangzhou J&H Chemical Co., Ltd.

J&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

1H-Benzimidazole-1-butanoicacid, 2,3-dihydro-2-oxo-

Cas:3273-68-5

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

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

2,3-Dihydro-2-oxo-1H-benzimidazole-1-butyric acid

Cas:3273-68-5

Min.Order:10 Gram

FOB Price: $100.0

Type:Lab/Research institutions

inquiry

Shanghai Minstar Chemical Co., Ltd

Product Name: 2-Oxo-1-benzimidazolinebutyric Acid Synonyms: 4-(2-OXO-2,3-DIHYDROBENZOIMIDAZOL-1-YL)BUTYRIC ACID;4-(2-oxo-2,3-dihydro-1H-1,3-benzimidazol-1-yl)butanoic acid;4-2-oxo-2,3-hihydro-1H-benzimidazol-1-yl)butanoic acid;2-Oxo-1-benzimida

2-Oxo-1-benzimidazolinebutyric Acid

Cas:3273-68-5

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Hangzhou Huarong Pharm Co., Ltd.

We Huarong Pharm can provide Customized Synthesis & Process R&D & APIs and intermediates Production & Quality Research & Registration Application, especially our GMP validation service which complies with SFDA, FDA, WHO and EU EMPA. O

1H-BENZIMIDAZOLE-1-BUTANOIC ACID, 2,3-DIHYDRO-2-OXO

Cas:3273-68-5

Min.Order:0

Negotiable

Type:Trading Company

inquiry

Shandong Mopai Biotechnology Co., LTD

Shandong Mopai Biotechnology 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 chemicals. W

1H-BENZIMIDAZOLE-1-BUTANOIC ACID, 2,3-DIHYDRO-2-OXO

Cas:3273-68-5

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Hunan chemfish Pharmaceutical co.,Ltd

Appearance:95%+ Package:R&D,Pilot run Transportation:per client require Port:Express ,Air, Sea

4-(2-Oxo-3H-benzimidazol-1-yl)butanoic acid

Cas:3273-68-5

Min.Order:0

Negotiable

Type:Manufacturers

inquiry

Suzhou Health Chemicals Co., Ltd.

High quality,stable supply chain.Appearance:white/off-white or light yellow Storage:Store in cool and dry place, keep away from strong light and heat. Package:aluminum bottle,glass bottle,PTFE bottle,cardboard drum Application:This product can be use

2-Oxo-1-benzimidazolinebutyric acid

Cas:3273-68-5

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

HANGZHOU YUNUO CHEMICAL CO.,LTD

Superior quality, moderate price & quick delivery. Appearance:white powder Storage:Stored in cool, dry and ventilation place; Away from fire and heat Package:25kg/drum, or as per your request. Application:Used as Pharmaceutical Intermediates Tr

1H-Benzimidazole-1-butanoicacid, 2,3-dihydro-2-oxo-

Cas:3273-68-5

Min.Order:1 Gram

Negotiable

Type:Trading Company

inquiry

Shanghai Finebiotech Co.,Ltd.

Shanghai Finebiotech Co.,Ltd.was established in 2020, which providing professional chemical services. As a customer-oriented company, we have distinguished ourself from others in providing worldwide customers with cost-effective and efficient service

4-(2-oxo-2,3-dihydro-1H-1,3-benzodiazol-1-yl)butanoic acid

Cas:3273-68-5

Min.Order:0

Negotiable

Type:Trading Company

inquiry

Kono Chem Co.,Ltd

high purity lowest priceAppearance:solid or liquid Storage:in sealed air resistant place Package:drum and bag Application:for pharma use Transportation:by sea or air Port:Beijing or Guangzhou

4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)butanoic acid

Cas:3273-68-5

Min.Order:0

Negotiable

Type:Other

inquiry

Hangzhou Dingyan Chem Co., Ltd

R & D enterprises have their own stock in stockAppearance:To be subject to the object Package:Customized Application:pharmaceutical intermediates Transportation:Air Port:Shanghai;Guangzhou

1H-BenziMidazole-1-butanoic acid, 2,3-dihydro-2-oxo-

Cas:3273-68-5

Min.Order:0

Negotiable

Type:Manufacturers

inquiry

Hubei Taiho Chemical Co.,LTD

TAIHO Unique Advantages:1.We're factory2.Free samples available3.Commodity inspection can be done4.ISO9001,Kosher certifications5.10 years experiences Storage:Store in cool &dry place Package:aluminium foil bag/fiber can/plastic drum Application:comp

4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)butanoic acid

Cas:3273-68-5

Min.Order:0

Negotiable

Type:Manufacturers

inquiry

Antimex Chemical Limied

Ansciep Chemical is a professional enterprise manufacturing and distributing fine chemicals and speciality chemicals. We have been dedicated to heterocycle compounds and phenyl rings for tens of years. This is our mature product for export. Our quali

1H-Benzimidazole-1-butanoicacid, 2,3-dihydro-2-oxo-

Cas:3273-68-5

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Guangdong Juda Chemical Industrial Co.,Limited

Factory supply high purity low priceAppearance:solid or liquid Storage:sealed in cool and dry place Package:As customer's requested Application:Pharma Intermediate Transportation:by courier/air/sea Port:Any port in China

2-Oxo-;Buzolic acid;Buzolic acid CAS No.3273-68-5

Cas:3273-68-5

Min.Order:0

Negotiable

Type:Trading Company

inquiry

HANGZHOU TIANYE CHEMICALS CO., LTD.

"HANGZHOU TIANYE CHEMICALS Co.LTD , Located in Eastern Science and Innovation Park Hangzhou .We are a high-tech enterprise specialized in technical research and development, production, development and trade of chemical products. We supply Multiple s

4-(2-oxo-3H-benzimidazol-1-yl)butanoic acid

Cas:3273-68-5

Min.Order:0

Negotiable

Type:Trading Company

inquiry

Hangzhou Fandachem Co.,Ltd

1H-Benzimidazole-1-butanoicacid, 2,3-dihydro-2-oxo-Appearance:white crystalline powder Storage:Store in dry, dark and ventilated place Package:25KG drum Application:pharmaceutical intermediate Transportation:by air, by sea, by express

1H-Benzimidazole-1-butanoicacid, 2,3-dihydro-2-oxo-

Cas:3273-68-5

Min.Order:0

Negotiable

Type:Other

inquiry

Hangzhou Sartort Biopharma Co., Ltd

Best quality with low priceAppearance:White solid Storage:ln stock Package:25kg/Barrel Application:Chemicals Transportation:Express/Sea/Air Port:Shanghai

4-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)butanoicacid

Cas:3273-68-5

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Henan Kanbei Chemical Co.,LTD

factory?direct?saleAppearance:White powder Storage:Sealed and preserved Package:200/Kilograms Application:healing drugs Transportation:By sea Port:Shanghai/tianjin

1H-BENZIMIDAZOLE-1-BUTANOIC ACID, 2,3-DIHYDRO-2-OXO

Cas:3273-68-5

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Synthetic route

4-(3-isopropenyl-2-oxo-2,3-dihydro-benzoimidazol-1-yl)-butyric acid
52099-78-2

4-(3-isopropenyl-2-oxo-2,3-dihydro-benzoimidazol-1-yl)-butyric acid

4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid
3273-68-5

4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid

Conditions
ConditionsYield
With hydrogenchloride In water at 100℃; for 6h;100%
With hydrogenchloride In 1,2-dimethoxyethane96%
With hydrogenchloride In tetrahydrofuran; water for 2h;
With hydrogenchloride; water In tetrahydrofuran for 2h;
1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one
52099-72-6

1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one

methyl 4-chlorobutyrate
3153-37-5

methyl 4-chlorobutyrate

4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid
3273-68-5

4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid

Conditions
ConditionsYield
Stage #1: 1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one; methyl 4-chlorobutyrate With tetrabutylammomium bromide; potassium carbonate; potassium iodide In dimethyl sulfoxide at 110 - 115℃;
Stage #2: With water; sodium hydroxide at 95 - 100℃; for 6h;
Stage #3: With hydrogenchloride In water at 80 - 85℃;
95%
4-butanolide
96-48-0

4-butanolide

sodium salt of N-isopropenylbenzimidazolin-2-one
84461-86-9

sodium salt of N-isopropenylbenzimidazolin-2-one

4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid
3273-68-5

4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 160 - 170℃; for 2h;30%
sodium salt of N-isopropenylbenzimidazolin-2-one
84461-86-9

sodium salt of N-isopropenylbenzimidazolin-2-one

4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid
3273-68-5

4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 2) 4 N hydrochloric acid / 1) DMF, 150 deg C to 160 deg C, 2 h, 2) water
2: 100 percent / 4 N HCl / H2O / 6 h / 100 °C
View Scheme
ethyl 2,3-dihydro-2-oxo-1H-benzimidazol-1-butanoate

ethyl 2,3-dihydro-2-oxo-1H-benzimidazol-1-butanoate

4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid
3273-68-5

4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid

Conditions
ConditionsYield
With sodium hydroxide In methanol; water
1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one
52099-72-6

1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one

4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid
3273-68-5

4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: potassium carbonate / acetone / 18 h / Heating / reflux
2.1: sodium hydroxide; water / tetrahydrofuran / 20 °C / Heating / reflux
2.2: 0.5 h / 2 °C
3.1: hydrogenchloride; water / tetrahydrofuran / 2 h
View Scheme
1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid
3273-68-5

4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / xylene / 60.5 h / 120 - 150 °C
2.1: potassium carbonate / acetone / 18 h / Heating / reflux
3.1: sodium hydroxide; water / tetrahydrofuran / 20 °C / Heating / reflux
3.2: 0.5 h / 2 °C
4.1: hydrogenchloride; water / tetrahydrofuran / 2 h
View Scheme
ethyl 2,3-dihydro-3-(1-methyl-ethenyl)-2-oxo-1H-benzimidazol-1-butanoate
116199-87-2

ethyl 2,3-dihydro-3-(1-methyl-ethenyl)-2-oxo-1H-benzimidazol-1-butanoate

4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid
3273-68-5

4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hydroxide; water / tetrahydrofuran / 20 °C / Heating / reflux
1.2: 0.5 h / 2 °C
2.1: hydrogenchloride; water / tetrahydrofuran / 2 h
View Scheme
4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid
3273-68-5

4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid

5,6-dihydroimidazo[4,5,1-jk][1]benzazepin-2,7-[1H,4H]-dione
92260-81-6

5,6-dihydroimidazo[4,5,1-jk][1]benzazepin-2,7-[1H,4H]-dione

Conditions
ConditionsYield
With aluminium trichloride; thionyl chloride 2.) 1,2-dichloroethane; Yield given. Multistep reaction;
Multi-step reaction with 2 steps
1.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 10 - 20 °C / Industry scale; Inert atmosphere
2.1: aluminum (III) chloride / dichloromethane / 58 - 60 °C / 2025.2 Torr / Industry scale
2.2: 5 - 20 °C / Industry scale
View Scheme
Stage #1: 4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid With thionyl chloride In dichloromethane at 20℃; for 2h;
Stage #2: With aluminum (III) chloride In dichloromethane at 20℃; Heating / reflux;
4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid
3273-68-5

4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid

chloro 2,3-dihydro-2-oxo-1H-benzimidazol-1-butanoate
1021910-67-7

chloro 2,3-dihydro-2-oxo-1H-benzimidazol-1-butanoate

Conditions
ConditionsYield
With thionyl chloride In dichloromethane at 20 - 25℃; for 2h;
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 10 - 20℃; for 2 - 6h; Product distribution / selectivity;
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 10 - 20℃; Industry scale; Inert atmosphere;
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 10 - 20℃; Industry scale; Inert atmosphere;
4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid
3273-68-5

4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid

4,5,6,7-tetrahydro-6-hydroxyimino-imidazo[4,5,1-jk]-[1]-benzazepine-2,7(1H,6H)-dione
92260-82-7

4,5,6,7-tetrahydro-6-hydroxyimino-imidazo[4,5,1-jk]-[1]-benzazepine-2,7(1H,6H)-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 10 - 20 °C / Industry scale; Inert atmosphere
2.1: aluminum (III) chloride / dichloromethane / 58 - 60 °C / 2025.2 Torr / Industry scale
2.2: 5 - 20 °C / Industry scale
3.1: hydrogenchloride; sodium nitrite / N,N-dimethyl-formamide / 1.5 h / 48 - 65 °C / Industry scale
View Scheme
Multi-step reaction with 2 steps
1.1: thionyl chloride / dichloromethane / 2 h / 20 °C
1.2: 20 °C / Heating / reflux
2.1: hydrogenchloride; t-butylnitrite; acetic acid / 1,4-dioxane / 3 h / 20 °C
View Scheme
4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid
3273-68-5

4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid

trans-7-amino-6-hydroxy-6,7,8,9-tetrahydro-2H-2,9a-diazabenzo[cd]azulen-1-one potassium salt

trans-7-amino-6-hydroxy-6,7,8,9-tetrahydro-2H-2,9a-diazabenzo[cd]azulen-1-one potassium salt

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 10 - 20 °C / Industry scale; Inert atmosphere
2.1: aluminum (III) chloride / dichloromethane / 58 - 60 °C / 2025.2 Torr / Industry scale
2.2: 5 - 20 °C / Industry scale
3.1: hydrogenchloride; sodium nitrite / N,N-dimethyl-formamide / 1.5 h / 48 - 65 °C / Industry scale
4.1: potassium hydroxide / water / 40 °C / Industry scale; Inert atmosphere
4.2: 40 °C / 6000.6 Torr / Industry scale
View Scheme
4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid
3273-68-5

4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid

trans-7-[isopropylimino]-6-hydroxy-6,7,8,9-tetrahydro-2H-2,9a-diazabenzo[cd]azulen-1-one

trans-7-[isopropylimino]-6-hydroxy-6,7,8,9-tetrahydro-2H-2,9a-diazabenzo[cd]azulen-1-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 10 - 20 °C / Industry scale; Inert atmosphere
2.1: aluminum (III) chloride / dichloromethane / 58 - 60 °C / 2025.2 Torr / Industry scale
2.2: 5 - 20 °C / Industry scale
3.1: hydrogenchloride; sodium nitrite / N,N-dimethyl-formamide / 1.5 h / 48 - 65 °C / Industry scale
4.1: potassium hydroxide / water / 40 °C / Industry scale; Inert atmosphere
4.2: 40 °C / 6000.6 Torr / Industry scale
5.1: acetic acid / water / 15 - 30 °C / pH 7.5 / Industry scale
View Scheme
4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid
3273-68-5

4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid

trans-4,5,6,7-tetrahydro-7-hydroxy-6-[(1-methylethyl)amino]imidazo[4,5,1-jk][1]benzazepin-2(1H)-one acetate

trans-4,5,6,7-tetrahydro-7-hydroxy-6-[(1-methylethyl)amino]imidazo[4,5,1-jk][1]benzazepin-2(1H)-one acetate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 10 - 20 °C / Industry scale; Inert atmosphere
2.1: aluminum (III) chloride / dichloromethane / 58 - 60 °C / 2025.2 Torr / Industry scale
2.2: 5 - 20 °C / Industry scale
3.1: hydrogenchloride; sodium nitrite / N,N-dimethyl-formamide / 1.5 h / 48 - 65 °C / Industry scale
4.1: potassium hydroxide / water / 40 °C / Industry scale; Inert atmosphere
4.2: 40 °C / 6000.6 Torr / Industry scale
5.1: acetic acid / water / 15 - 30 °C / pH 7.5 / Industry scale
6.1: hydrogen / 5%-palladium/activated carbon / water / 2.5 h / 15 - 70 °C / 6000.6 Torr / Industry scale
6.2: 30 - 70 °C / pH 6.8 / Industry scale
View Scheme
4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid
3273-68-5

4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid

trans-(+/-)-4,5,6,7-tetrahydro-7-hydroxy-6-[(1-methylethyl)amino]-imidazo[4,5,1-jk][1]benzazepin-2(1H)-one

trans-(+/-)-4,5,6,7-tetrahydro-7-hydroxy-6-[(1-methylethyl)amino]-imidazo[4,5,1-jk][1]benzazepin-2(1H)-one

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 10 - 20 °C / Industry scale; Inert atmosphere
2.1: aluminum (III) chloride / dichloromethane / 58 - 60 °C / 2025.2 Torr / Industry scale
2.2: 5 - 20 °C / Industry scale
3.1: hydrogenchloride; sodium nitrite / N,N-dimethyl-formamide / 1.5 h / 48 - 65 °C / Industry scale
4.1: potassium hydroxide / water / 40 °C / Industry scale; Inert atmosphere
4.2: 40 °C / 6000.6 Torr / Industry scale
5.1: acetic acid / water / 15 - 30 °C / pH 7.5 / Industry scale
6.1: hydrogen / 5%-palladium/activated carbon / water / 2.5 h / 15 - 70 °C / 6000.6 Torr / Industry scale
6.2: 30 - 70 °C / pH 6.8 / Industry scale
7.1: sodium hydroxide / water / 50 °C / pH 11 / Industry scale; Inert atmosphere
View Scheme
4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid
3273-68-5

4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid

trans-(+/-)-4,5,6,7-tetrahydro-7-hydroxy-6-[(1-methylethyl)amino]-imidazo[4,5,1-jk][1]benzazepin-2(1H)-one hydrochloride

trans-(+/-)-4,5,6,7-tetrahydro-7-hydroxy-6-[(1-methylethyl)amino]-imidazo[4,5,1-jk][1]benzazepin-2(1H)-one hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 10 - 20 °C / Industry scale; Inert atmosphere
2.1: aluminum (III) chloride / dichloromethane / 58 - 60 °C / 2025.2 Torr / Industry scale
2.2: 5 - 20 °C / Industry scale
3.1: hydrogenchloride; sodium nitrite / N,N-dimethyl-formamide / 1.5 h / 48 - 65 °C / Industry scale
4.1: potassium hydroxide / water / 40 °C / Industry scale; Inert atmosphere
4.2: 40 °C / 6000.6 Torr / Industry scale
5.1: acetic acid / water / 15 - 30 °C / pH 7.5 / Industry scale
6.1: hydrogen / 5%-palladium/activated carbon / water / 2.5 h / 15 - 70 °C / 6000.6 Torr / Industry scale
6.2: 30 - 70 °C / pH 6.8 / Industry scale
7.1: sodium hydroxide / water / 50 °C / pH 11 / Industry scale; Inert atmosphere
8.1: hydrogenchloride / water / 10 °C
View Scheme
4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid
3273-68-5

4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid

A

(6R,7R)-7-hydroxy-6-[((S)-1-methyl-3-phenylpropyl)amino]-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(6R,7R)-7-hydroxy-6-[((S)-1-methyl-3-phenylpropyl)amino]-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

B

(6S,7S)-7-hydroxy-6-[((R)-1-methyl-3-phenylpropyl)amino]-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(6S,7S)-7-hydroxy-6-[((R)-1-methyl-3-phenylpropyl)amino]-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: thionyl chloride / dichloromethane / 2 h / 20 °C
1.2: 20 °C / Heating / reflux
2.1: hydrogenchloride; t-butylnitrite; acetic acid / 1,4-dioxane / 3 h / 20 °C
3.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / methanol / 3 h / 20 °C / 1137.76 Torr
4.1: sodium tetrahydroborate / methanol / 18.5 h / 0 - 20 °C
5.1: methanol / 20 - 80 °C / Microwave irradiation
5.3: Amberlyst.(R). 15 ion-exchange resin
View Scheme
4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid
3273-68-5

4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid

A

(E)-(6R,7R)-6-{[(R)-3-(2-fluorophenyl)-1-methylprop-2-en-1-yl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(E)-(6R,7R)-6-{[(R)-3-(2-fluorophenyl)-1-methylprop-2-en-1-yl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

B

(6R,7R)-(E)-6-{[(S)-3-(2-fluorophenyl)-1-methylprop-2-en-1-yl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(6R,7R)-(E)-6-{[(S)-3-(2-fluorophenyl)-1-methylprop-2-en-1-yl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

C

(E)-(6S,7S)-6-{[(R)-3-(2-fluorophenyl)-1-methylprop-2-en-1-yl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(E)-(6S,7S)-6-{[(R)-3-(2-fluorophenyl)-1-methylprop-2-en-1-yl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

D

(E)-(6S,7S)-6-{[(S)-3-(2-fluorophenyl)-1-methylprop-2-en-1-yl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(E)-(6S,7S)-6-{[(S)-3-(2-fluorophenyl)-1-methylprop-2-en-1-yl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: thionyl chloride / dichloromethane / 2 h / 20 °C
1.2: 20 °C / Heating / reflux
2.1: hydrogenchloride; t-butylnitrite; acetic acid / 1,4-dioxane / 3 h / 20 °C
3.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / methanol / 3 h / 20 °C / 1137.76 Torr
4.1: sodium tetrahydroborate / methanol / 18.5 h / 0 - 20 °C
5.1: triethylamine / methanol / 1 h / 20 °C
5.2: 72 h
View Scheme
4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid
3273-68-5

4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid

A

(6S,7S)-7-hydroxy-6-{[(R)-3-(4-hydroxyphenyl)-1-methylpropyl]amino}-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(6S,7S)-7-hydroxy-6-{[(R)-3-(4-hydroxyphenyl)-1-methylpropyl]amino}-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

B

(6S,7S)-7-hydroxy-6-{[(S)-3-(4-hydroxyphenyl)-1-methylpropyl]amino}-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(6S,7S)-7-hydroxy-6-{[(S)-3-(4-hydroxyphenyl)-1-methylpropyl]amino}-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

C

(6R,7R)-7-hydroxy-6-{[(R)-3-(4-hydroxyphenyl)-1-methylpropyl]amino}-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(6R,7R)-7-hydroxy-6-{[(R)-3-(4-hydroxyphenyl)-1-methylpropyl]amino}-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

D

(6R,7R)-7-hydroxy-6-{[(S)-3-(4-hydroxyphenyl)-1-methylpropyl]amino}-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(6R,7R)-7-hydroxy-6-{[(S)-3-(4-hydroxyphenyl)-1-methylpropyl]amino}-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: thionyl chloride / dichloromethane / 2 h / 20 °C
1.2: 20 °C / Heating / reflux
2.1: hydrogenchloride; t-butylnitrite; acetic acid / 1,4-dioxane / 3 h / 20 °C
3.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / methanol / 3 h / 20 °C / 1137.76 Torr
4.1: sodium tetrahydroborate / methanol / 18.5 h / 0 - 20 °C
5.1: triethylamine / methanol / 60 h / 20 °C
5.2: 18 h / 0 - 20 °C
View Scheme
4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid
3273-68-5

4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid

(6R,7R)-6-{[(R)-3-(4-aminophenyl)-1-methylpropyl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(6R,7R)-6-{[(R)-3-(4-aminophenyl)-1-methylpropyl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: thionyl chloride / dichloromethane / 2 h / 20 °C
1.2: 20 °C / Heating / reflux
2.1: hydrogenchloride; t-butylnitrite; acetic acid / 1,4-dioxane / 3 h / 20 °C
3.1: hydrogen / di-μ-chlorobis(norbornadiene)dirhodium(I) / methanol; water / 16 h / 80 °C / 15001.5 Torr
4.1: triethylamine / methanol / 0.33 h
4.2: 120 h / 60 °C
5.1: hydrogen / palladium 10% on activated carbon / methanol / 55 °C / 760.05 Torr
View Scheme
Multi-step reaction with 9 steps
1.1: thionyl chloride / dichloromethane / 2 h / 20 °C
1.2: 20 °C / Heating / reflux
2.1: hydrogenchloride; t-butylnitrite; acetic acid / 1,4-dioxane / 3 h / 20 °C
3.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / methanol / 3 h / 20 °C / 1137.76 Torr
4.1: sodium tetrahydroborate / methanol / 18.5 h / 0 - 20 °C
5.1: triethylamine / methanol / 1 h
6.1: diethylamine / isopropyl alcohol / Heating / reflux; Sonication
7.1: hydrogenchloride / 1,4-dioxane / 1 h / 20 °C
8.1: triethylamine / methanol / 0.33 h
8.2: 120 h / 60 °C
9.1: hydrogen / palladium 10% on activated carbon / methanol / 55 °C / 760.05 Torr
View Scheme
4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid
3273-68-5

4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid

(6S,7S)-7-hydroxy-6-{[(S)-3-(2-hydroxyphenyl)-1-methylpropyl]amino}-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one
1019769-22-2

(6S,7S)-7-hydroxy-6-{[(S)-3-(2-hydroxyphenyl)-1-methylpropyl]amino}-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: thionyl chloride / dichloromethane / 2 h / 20 °C
1.2: 20 °C / Heating / reflux
2.1: hydrogenchloride; t-butylnitrite; acetic acid / 1,4-dioxane / 3 h / 20 °C
3.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / methanol / 3 h / 20 °C / 1137.76 Torr
4.1: sodium tetrahydroborate / methanol / 18.5 h / 0 - 20 °C
5.1: triethylamine / methanol / 0.33 h
5.2: 40 h / 50 °C
View Scheme
Multi-step reaction with 5 steps
1.1: thionyl chloride / dichloromethane / 2 h / 20 °C
1.2: 20 °C / Heating / reflux
2.1: hydrogenchloride; t-butylnitrite; acetic acid / 1,4-dioxane / 3 h / 20 °C
3.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / methanol / 3 h / 20 °C / 1137.76 Torr
4.1: sodium tetrahydroborate / methanol / 18.5 h / 0 - 20 °C
5.1: potassium hydroxide / methanol / 0.33 h
5.2: 60 h / 60 °C
View Scheme
4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid
3273-68-5

4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid

A

(6R,7R)-7-hydroxy-6-{[(R)-3-(2-hydroxyphenyl)-1-methylpropyl]amino}-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one
1019768-88-7

(6R,7R)-7-hydroxy-6-{[(R)-3-(2-hydroxyphenyl)-1-methylpropyl]amino}-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

B

(6R,7R)-7-hydroxy-6-{[(S)-3-(2-hydroxyphenyl)-1-methylpropyl]amino}-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(6R,7R)-7-hydroxy-6-{[(S)-3-(2-hydroxyphenyl)-1-methylpropyl]amino}-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

C

7-hydroxy-6-{[3-(2-hydroxyphenyl)-1-methylpropyl]amino}-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

7-hydroxy-6-{[3-(2-hydroxyphenyl)-1-methylpropyl]amino}-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: thionyl chloride / dichloromethane / 2 h / 20 °C
1.2: 20 °C / Heating / reflux
2.1: hydrogenchloride; t-butylnitrite; acetic acid / 1,4-dioxane / 3 h / 20 °C
3.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / methanol / 3 h / 20 °C / 1137.76 Torr
4.1: sodium tetrahydroborate / methanol / 18.5 h / 0 - 20 °C
5.1: triethylamine / methanol / 0.33 h
5.2: 40 h / 50 °C
View Scheme
Multi-step reaction with 5 steps
1.1: thionyl chloride / dichloromethane / 2 h / 20 °C
1.2: 20 °C / Heating / reflux
2.1: hydrogenchloride; t-butylnitrite; acetic acid / 1,4-dioxane / 3 h / 20 °C
3.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / methanol / 3 h / 20 °C / 1137.76 Torr
4.1: sodium tetrahydroborate / methanol / 18.5 h / 0 - 20 °C
5.1: potassium hydroxide / methanol / 0.33 h
5.2: 60 h / 60 °C
View Scheme
4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid
3273-68-5

4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid

A

(6R,7R)-7-hydroxy-6-{[(R)-3-(2-hydroxyphenyl)-1,3-dimethylbutyl]amino}-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(6R,7R)-7-hydroxy-6-{[(R)-3-(2-hydroxyphenyl)-1,3-dimethylbutyl]amino}-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

B

(6R,7R)-7-hydroxy-6-{[(S)-3-(2-hydroxyphenyl)-1,3-dimethylbutyl]amino}-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(6R,7R)-7-hydroxy-6-{[(S)-3-(2-hydroxyphenyl)-1,3-dimethylbutyl]amino}-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

C

(6S,7S)-7-hydroxy-6-{[(R)-3-(2-hydroxyphenyl)-1,3-dimethylbutyl]amino}-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(6S,7S)-7-hydroxy-6-{[(R)-3-(2-hydroxyphenyl)-1,3-dimethylbutyl]amino}-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

D

(6S,7S)-7-hydroxy-6-{[(S)-3-(2-hydroxyphenyl)-1,3-dimethylbutyl]amino}-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(6S,7S)-7-hydroxy-6-{[(S)-3-(2-hydroxyphenyl)-1,3-dimethylbutyl]amino}-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: thionyl chloride / dichloromethane / 2 h / 20 °C
1.2: 20 °C / Heating / reflux
2.1: hydrogenchloride; t-butylnitrite; acetic acid / 1,4-dioxane / 3 h / 20 °C
3.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / methanol / 3 h / 20 °C / 1137.76 Torr
4.1: sodium tetrahydroborate / methanol / 18.5 h / 0 - 20 °C
5.1: triethylamine / methanol / 1 h / 20 °C
5.2: 108 h / 20 - 60 °C
View Scheme
4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid
3273-68-5

4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid

A

(6S,7S)-7-hydroxy-6-({(R)-3-[3-(hydroxymethyl)phenyl]-1-methylpropyl}amino)-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(6S,7S)-7-hydroxy-6-({(R)-3-[3-(hydroxymethyl)phenyl]-1-methylpropyl}amino)-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

B

(6S,7S)-7-hydroxy-6-({(S)-3-[3-(hydroxymethyl)phenyl]-1-methylpropyl}amino)-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(6S,7S)-7-hydroxy-6-({(S)-3-[3-(hydroxymethyl)phenyl]-1-methylpropyl}amino)-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

C

(6R,7R)-7-hydroxy-6-({(R)-3-[3-(hydroxymethyl)phenyl]-1-methylpropyl}amino)-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(6R,7R)-7-hydroxy-6-({(R)-3-[3-(hydroxymethyl)phenyl]-1-methylpropyl}amino)-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

D

(6R,7R)-7-hydroxy-6-({(S)-3-[3-(hydroxymethyl)phenyl]-1-methylpropyl}amino)-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(6R,7R)-7-hydroxy-6-({(S)-3-[3-(hydroxymethyl)phenyl]-1-methylpropyl}amino)-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: thionyl chloride / dichloromethane / 2 h / 20 °C
1.2: 20 °C / Heating / reflux
2.1: hydrogenchloride; t-butylnitrite; acetic acid / 1,4-dioxane / 3 h / 20 °C
3.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / methanol / 3 h / 20 °C / 1137.76 Torr
4.1: sodium tetrahydroborate / methanol / 18.5 h / 0 - 20 °C
5.1: triethylamine / methanol / 18 h / 20 °C
5.2: 1 h / 20 °C
5.3: Amberlyst.(R). 15 ion-exchange resin
6.1: hydrogen / platinum(IV) oxide / water; isopropyl alcohol / 0.5 h / 3102.97 Torr
View Scheme
4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid
3273-68-5

4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid

A

(6R,7R)-6-{[(R)-3-(5-fluoro-2-hydroxyphenyl)-1-methylpropyl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(6R,7R)-6-{[(R)-3-(5-fluoro-2-hydroxyphenyl)-1-methylpropyl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

B

(6R,7R)-6-{[(S)-3-(5-fluoro-2-hydroxyphenyl)-1-methylpropyl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(6R,7R)-6-{[(S)-3-(5-fluoro-2-hydroxyphenyl)-1-methylpropyl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

C

(6S,7S)-6-{[(R)-3-(5-fluoro-2-hydroxyphenyl)-1-methylpropyl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(6S,7S)-6-{[(R)-3-(5-fluoro-2-hydroxyphenyl)-1-methylpropyl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

D

(6S,7S)-6-{[(S)-3-(5-fluoro-2-hydroxyphenyl)-1-methylpropyl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(6S,7S)-6-{[(S)-3-(5-fluoro-2-hydroxyphenyl)-1-methylpropyl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: thionyl chloride / dichloromethane / 2 h / 20 °C
1.2: 20 °C / Heating / reflux
2.1: hydrogenchloride; t-butylnitrite; acetic acid / 1,4-dioxane / 3 h / 20 °C
3.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / methanol / 3 h / 20 °C / 1137.76 Torr
4.1: sodium tetrahydroborate / methanol / 18.5 h / 0 - 20 °C
5.1: triethylamine / methanol / 0.5 h / 50 °C
5.2: 18 h / 50 °C
View Scheme
4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid
3273-68-5

4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid

A

(6R,7R)-7-hydroxy-6-{[(R)-3-(2-hydroxy-3-methoxyphenyl)-1-methylpropyl]amino}-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(6R,7R)-7-hydroxy-6-{[(R)-3-(2-hydroxy-3-methoxyphenyl)-1-methylpropyl]amino}-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

B

(6R,7R)-7-hydroxy-6-{[(S)-3-(2-hydroxy-3-methoxyphenyl)-1-methylpropyl]amino}-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(6R,7R)-7-hydroxy-6-{[(S)-3-(2-hydroxy-3-methoxyphenyl)-1-methylpropyl]amino}-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

C

(6S,7S)-7-hydroxy-6-{[(R)-3-(2-hydroxy-3-methoxyphenyl)-1-methylpropyl]amino}-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(6S,7S)-7-hydroxy-6-{[(R)-3-(2-hydroxy-3-methoxyphenyl)-1-methylpropyl]amino}-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

D

(6S,7S)-7-hydroxy-6-{[(S)-3-(2-hydroxy-3-methoxyphenyl)-1-methylpropyl]amino}-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(6S,7S)-7-hydroxy-6-{[(S)-3-(2-hydroxy-3-methoxyphenyl)-1-methylpropyl]amino}-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: thionyl chloride / dichloromethane / 2 h / 20 °C
1.2: 20 °C / Heating / reflux
2.1: hydrogenchloride; t-butylnitrite; acetic acid / 1,4-dioxane / 3 h / 20 °C
3.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / methanol / 3 h / 20 °C / 1137.76 Torr
4.1: sodium tetrahydroborate / methanol / 18.5 h / 0 - 20 °C
5.1: triethylamine / methanol / 1 h
5.2: 18 h / 20 °C
View Scheme
4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid
3273-68-5

4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid

A

(6S,7S)-6-{[(R)-3-(3-chloro-2-hydroxyphenyl)-1-methylpropyl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(6S,7S)-6-{[(R)-3-(3-chloro-2-hydroxyphenyl)-1-methylpropyl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

B

(6S,7S)-6-{[(S)-3-(3-chloro-2-hydroxyphenyl)-1-methylpropyl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(6S,7S)-6-{[(S)-3-(3-chloro-2-hydroxyphenyl)-1-methylpropyl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

C

(6R,7R)-6-{[3-(3-chloro-2-hydroxyphenyl)-(1R)-1-methylpropyl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(6R,7R)-6-{[3-(3-chloro-2-hydroxyphenyl)-(1R)-1-methylpropyl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

D

(6R,7R)-6-{[(S)-3-(3-chloro-2-hydroxyphenyl)-1-methylpropyl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(6R,7R)-6-{[(S)-3-(3-chloro-2-hydroxyphenyl)-1-methylpropyl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: thionyl chloride / dichloromethane / 2 h / 20 °C
1.2: 20 °C / Heating / reflux
2.1: hydrogenchloride; t-butylnitrite; acetic acid / 1,4-dioxane / 3 h / 20 °C
3.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / methanol / 3 h / 20 °C / 1137.76 Torr
4.1: sodium tetrahydroborate / methanol / 18.5 h / 0 - 20 °C
5.1: triethylamine / methanol / 1 h / 20 °C
5.2: 120 h / 20 °C
View Scheme
4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid
3273-68-5

4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid

A

(6S,7S)-6-{[(R)-3-(2,3-dihydro-1-benzofuran-5-yl)-1-methylpropyl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(6S,7S)-6-{[(R)-3-(2,3-dihydro-1-benzofuran-5-yl)-1-methylpropyl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

B

(6S,7S)-6-{[(S)-3-(2,3-dihydro-1-benzofuran-5-yl)-1-methylpropyl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(6S,7S)-6-{[(S)-3-(2,3-dihydro-1-benzofuran-5-yl)-1-methylpropyl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

C

(6R,7R)-6-{[(R)-3-(2,3-dihydro-1-benzofuran-5-yl)-1-methylpropyl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(6R,7R)-6-{[(R)-3-(2,3-dihydro-1-benzofuran-5-yl)-1-methylpropyl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

D

(6R,7R)-6-{[(S)-3-(2,3-dihydro-1-benzofuran-5-yl)-1-methylpropyl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(6R,7R)-6-{[(S)-3-(2,3-dihydro-1-benzofuran-5-yl)-1-methylpropyl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: thionyl chloride / dichloromethane / 2 h / 20 °C
1.2: 20 °C / Heating / reflux
2.1: hydrogenchloride; t-butylnitrite; acetic acid / 1,4-dioxane / 3 h / 20 °C
3.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / methanol / 3 h / 20 °C / 1137.76 Torr
4.1: sodium tetrahydroborate / methanol / 18.5 h / 0 - 20 °C
5.1: triethylamine / methanol / 1 h / 20 °C
5.2: 60 h / 20 °C
View Scheme
4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid
3273-68-5

4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid

A

(6S,7S)-6-({(R)-3-[4-(cyclopropylmethoxy)phenyl]-1-methylpropyl}amino)-7-hydroxy-4,5,6,7-tetrahydro-imidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(6S,7S)-6-({(R)-3-[4-(cyclopropylmethoxy)phenyl]-1-methylpropyl}amino)-7-hydroxy-4,5,6,7-tetrahydro-imidazo[4,5,1-jk][1]benzazepin-2(1H)-one

B

(6S,7S)-6-({(S)-3-[4-(cyclopropylmethoxy)phenyl]-1-methylpropyl}amino)-7-hydroxy-4,5,6,7-tetrahydro-imidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(6S,7S)-6-({(S)-3-[4-(cyclopropylmethoxy)phenyl]-1-methylpropyl}amino)-7-hydroxy-4,5,6,7-tetrahydro-imidazo[4,5,1-jk][1]benzazepin-2(1H)-one

C

(6R,7R)-6-({(R)-3-[4-(cyclopropylmethoxy)phenyl]-1-methylpropyl}amino)-7-hydroxy-4,5,6,7-tetrahydro-imidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(6R,7R)-6-({(R)-3-[4-(cyclopropylmethoxy)phenyl]-1-methylpropyl}amino)-7-hydroxy-4,5,6,7-tetrahydro-imidazo[4,5,1-jk][1]benzazepin-2(1H)-one

D

(6R,7R)-6-({(S)-3-[4-(cyclopropylmethoxy)phenyl]-1-methylpropyl}amino)-7-hydroxy-4,5,6,7-tetrahydro-imidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(6R,7R)-6-({(S)-3-[4-(cyclopropylmethoxy)phenyl]-1-methylpropyl}amino)-7-hydroxy-4,5,6,7-tetrahydro-imidazo[4,5,1-jk][1]benzazepin-2(1H)-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: thionyl chloride / dichloromethane / 2 h / 20 °C
1.2: 20 °C / Heating / reflux
2.1: hydrogenchloride; t-butylnitrite; acetic acid / 1,4-dioxane / 3 h / 20 °C
3.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / methanol / 3 h / 20 °C / 1137.76 Torr
4.1: sodium tetrahydroborate / methanol / 18.5 h / 0 - 20 °C
5.1: potassium hydroxide / methanol
5.2: 48.5 h / 0 - 20 °C
5.3: Amberlyst.(R). 15 ion-exchange resin
View Scheme
4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid
3273-68-5

4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid

A

(6R,7R)-6-{[(R)-3-(3,5-difluoro-2-hydroxyphenyl)-1-methylpropyl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(6R,7R)-6-{[(R)-3-(3,5-difluoro-2-hydroxyphenyl)-1-methylpropyl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

B

(6R,7R)-6-{[(S)-3-(3,5-difluoro-2-hydroxyphenyl)-1-methylpropyl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(6R,7R)-6-{[(S)-3-(3,5-difluoro-2-hydroxyphenyl)-1-methylpropyl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

C

(6S,7S)-6-{[(R)-3-(3,5-difluoro-2-hydroxyphenyl)-1-methylpropyl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(6S,7S)-6-{[(R)-3-(3,5-difluoro-2-hydroxyphenyl)-1-methylpropyl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

D

(6S,7S)-6-{[(S)-3-(3,5-difluoro-2-hydroxyphenyl)-1-methylpropyl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(6S,7S)-6-{[(S)-3-(3,5-difluoro-2-hydroxyphenyl)-1-methylpropyl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: thionyl chloride / dichloromethane / 2 h / 20 °C
1.2: 20 °C / Heating / reflux
2.1: hydrogenchloride; t-butylnitrite; acetic acid / 1,4-dioxane / 3 h / 20 °C
3.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / methanol / 3 h / 20 °C / 1137.76 Torr
4.1: sodium tetrahydroborate / methanol / 18.5 h / 0 - 20 °C
5.1: triethylamine / methanol / 0.42 h
5.2: 80 h / 50 °C
View Scheme
4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid
3273-68-5

4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid

A

(6R,7R)-6-{[(R)-3-(4,5-difluoro-2-hydroxyphenyl)-1-methylpropyl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(6R,7R)-6-{[(R)-3-(4,5-difluoro-2-hydroxyphenyl)-1-methylpropyl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

B

(6R,7R)-6-{[(S)-3-(4,5-difluoro-2-hydroxyphenyl)-1-methylpropyl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(6R,7R)-6-{[(S)-3-(4,5-difluoro-2-hydroxyphenyl)-1-methylpropyl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

C

(6S,7S)-6-{[(R)-3-(4,5-difluoro-2-hydroxyphenyl)-1-methylpropyl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(6S,7S)-6-{[(R)-3-(4,5-difluoro-2-hydroxyphenyl)-1-methylpropyl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

D

(6S,7S)-6-{[(S)-3-(4,5-difluoro-2-hydroxyphenyl)-1-methylpropyl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(6S,7S)-6-{[(S)-3-(4,5-difluoro-2-hydroxyphenyl)-1-methylpropyl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: thionyl chloride / dichloromethane / 2 h / 20 °C
1.2: 20 °C / Heating / reflux
2.1: hydrogenchloride; t-butylnitrite; acetic acid / 1,4-dioxane / 3 h / 20 °C
3.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / methanol / 3 h / 20 °C / 1137.76 Torr
4.1: sodium tetrahydroborate / methanol / 18.5 h / 0 - 20 °C
5.1: triethylamine / methanol / 1 h / 45 °C
5.2: 120 h / 45 °C
View Scheme
4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid
3273-68-5

4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid

(6R,7R)-6-{[3-(2-chloro-3-hydroxyphenyl)-1-methylpropyl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

(6R,7R)-6-{[3-(2-chloro-3-hydroxyphenyl)-1-methylpropyl]amino}-7-hydroxy-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1]benzazepin-2(1H)-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: thionyl chloride / dichloromethane / 2 h / 20 °C
1.2: 20 °C / Heating / reflux
2.1: hydrogenchloride; t-butylnitrite; acetic acid / 1,4-dioxane / 3 h / 20 °C
3.1: hydrogen / di-μ-chlorobis(norbornadiene)dirhodium(I) / methanol; water / 16 h / 80 °C / 15001.5 Torr
4.1: triethylamine / methanol / 0.33 h
4.2: 18 h / 60 °C
View Scheme
Multi-step reaction with 8 steps
1.1: thionyl chloride / dichloromethane / 2 h / 20 °C
1.2: 20 °C / Heating / reflux
2.1: hydrogenchloride; t-butylnitrite; acetic acid / 1,4-dioxane / 3 h / 20 °C
3.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / methanol / 3 h / 20 °C / 1137.76 Torr
4.1: sodium tetrahydroborate / methanol / 18.5 h / 0 - 20 °C
5.1: triethylamine / methanol / 1 h
6.1: diethylamine / isopropyl alcohol / Heating / reflux; Sonication
7.1: hydrogenchloride / 1,4-dioxane / 1 h / 20 °C
8.1: triethylamine / methanol / 0.33 h
8.2: 18 h / 60 °C
View Scheme

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