(3'R,4'S)-3'-{[2-chloro-5-(2-methoxy-ethyl)-benzyl]cyclopropylcarbamoyl}-6-[2-(2,6-dichloro-4-methyl-phenoxy)ethoxy]-3',4',5',6'-tetrahydro-2'H-[3,4']bipyridinyl-1'-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (3'R,4'S)-3'-{[2-chloro-5-(2-methoxy-ethyl)-benzyl]cyclopropylcarbamoyl}-6-[2-(2,6-dichloro-4-methyl-phenoxy)ethoxy]-3',4',5',6'-tetrahydro-2'H-[3,4']bipyridinyl-1'-carboxylic acid tert-butyl ester
• CAS No.: 1206625-73-1
• Molecular Formula: C₃₈H₄₆Cl₃N₃O₆
• Molecular Weight: 747.159

Synonyms:(3'R,4'S)-3'-{[2-chloro-5-(2-methoxy-ethyl)-benzyl]cyclopropylcarbamoyl}-6-[2-(2,6-dichloro-4-methyl-phenoxy)ethoxy]-3',4',5',6'-tetrahydro-2'H-[3,4']bipyridinyl-1'-carboxylic acid tert-butyl ester

Chemical Property of (3'R,4'S)-3'-{[2-chloro-5-(2-methoxy-ethyl)-benzyl]cyclopropylcarbamoyl}-6-[2-(2,6-dichloro-4-methyl-phenoxy)ethoxy]-3',4',5',6'-tetrahydro-2'H-[3,4']bipyridinyl-1'-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of (3'R,4'S)-3'-{[2-chloro-5-(2-methoxy-ethyl)-benzyl]cyclopropylcarbamoyl}-6-[2-(2,6-dichloro-4-methyl-phenoxy)ethoxy]-3',4',5',6'-tetrahydro-2'H-[3,4']bipyridinyl-1'-carboxylic acid tert-butyl ester

There total 18 articles about (3'R,4'S)-3'-{[2-chloro-5-(2-methoxy-ethyl)-benzyl]cyclopropylcarbamoyl}-6-[2-(2,6-dichloro-4-methyl-phenoxy)ethoxy]-3',4',5',6'-tetrahydro-2'H-[3,4']bipyridinyl-1'-carboxylic acid tert-butyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

N-[2-chloro-5-(2-methoxyethyl)benzyl]cyclopropanamine (921630-23-1) + (3'R,4'S)-6-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]-3',4',5',6'-tetrahydro-2'H-[3,4']bipyridinyl-1',3'-dicarboxylic acid 1'-tert-butyl ester (1026786-82-2) + p-toluenesulfonyl chloride (98-59-9) → (3'R,4'S)-3'-{[2-chloro-5-(2-methoxy-ethyl)-benzyl]cyclopropylcarbamoyl}-6-[2-(2,6-dichloro-4-methyl-phenoxy)ethoxy]-3',4',5',6'-tetrahydro-2'H-[3,4']bipyridinyl-1'-carboxylic acid tert-butyl ester (1206625-73-1)

Guidance literature:

(3'R,4'S)-6-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]-3',4',5',6'-tetrahydro-2'H-[3,4']bipyridinyl-1',3'-dicarboxylic acid 1'-tert-butyl ester; p-toluenesulfonyl chloride; With 1-methyl-1H-imidazole; In 2-methyltetrahydrofuran; at -20 - -5 ℃; for 3.25h; Cooling with dry ice/iso-propanol bath;

N-[2-chloro-5-(2-methoxyethyl)benzyl]cyclopropanamine; In 2-methyltetrahydrofuran; acetonitrile; at -5 - 20 ℃; for 16.0833h; Inert atmosphere;

Reference yield:

2-[2-(2,6-dichloro-4-methyl-phenoxy)ethoxy]-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridine (1206625-60-6) → (3'R,4'S)-3'-{[2-chloro-5-(2-methoxy-ethyl)-benzyl]cyclopropylcarbamoyl}-6-[2-(2,6-dichloro-4-methyl-phenoxy)ethoxy]-3',4',5',6'-tetrahydro-2'H-[3,4']bipyridinyl-1'-carboxylic acid tert-butyl ester (1206625-73-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / 1,2-dimethoxyethane; water / 1.08 h / 50 - 83 °C / Inert atmosphere; Large scale reaction

2.1: tetrafluoroboric acid diethyl ether; [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); Josiphos SL-J₂₁₂-1; hydrogen / tetrahydrofuran; dichloromethane / 20 h / 15 °C / 41372.9 Torr / Autoclave; Large scale reaction

3.1: sodium ethanolate / ethanol / 1 h / 70 °C / Inert atmosphere; Large scale reaction

3.2: 1 h / 70 °C / Inert atmosphere; Large scale reaction

4.1: 1-methyl-1H-imidazole / 2-methyltetrahydrofuran; acetonitrile / 3.25 h / -20 - -5 °C / Inert atmosphere; Large scale reaction

5.1: 2-methyltetrahydrofuran; acetonitrile / 16 h / 20 °C / Inert atmosphere; Large scale reaction

With 1-methyl-1H-imidazole; tetrafluoroboric acid diethyl ether; [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); tetrakis(triphenylphosphine) palladium⁽⁰⁾; Josiphos SL-J₂₁₂-1; hydrogen; sodium ethanolate; sodium carbonate; In tetrahydrofuran; 2-methyltetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; water; acetonitrile; 1.1: Suzuki coupling;

DOI:10.1021/jo102070e

Reference yield:

p-cresol (106-44-5) → (3'R,4'S)-3'-{[2-chloro-5-(2-methoxy-ethyl)-benzyl]cyclopropylcarbamoyl}-6-[2-(2,6-dichloro-4-methyl-phenoxy)ethoxy]-3',4',5',6'-tetrahydro-2'H-[3,4']bipyridinyl-1'-carboxylic acid tert-butyl ester (1206625-73-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: sodium hypochlorite / water; acetonitrile / 0 - 18 °C / Inert atmosphere; Large scale reaction

2.1: 1-methyl-1H-imidazole / N,N-dimethyl acetamide / 2.25 h / 110 °C / Inert atmosphere; Large scale reaction

2.2: 0.5 h / 20 °C / Inert atmosphere; Large scale reaction

2.3: 80 - 90 °C / Inert atmosphere; Large scale reaction

3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate / N,N-dimethyl acetamide / 20 h / 80 - 85 °C / Inert atmosphere; Large scale reaction

4.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / 1,2-dimethoxyethane; water / 1.08 h / 50 - 83 °C / Inert atmosphere; Large scale reaction

5.1: tetrafluoroboric acid diethyl ether; [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); Josiphos SL-J₂₁₂-1; hydrogen / tetrahydrofuran; dichloromethane / 20 h / 15 °C / 41372.9 Torr / Autoclave; Large scale reaction

6.1: sodium ethanolate / ethanol / 1 h / 70 °C / Inert atmosphere; Large scale reaction

6.2: 1 h / 70 °C / Inert atmosphere; Large scale reaction

7.1: 1-methyl-1H-imidazole / 2-methyltetrahydrofuran; acetonitrile / 3.25 h / -20 - -5 °C / Inert atmosphere; Large scale reaction

8.1: 2-methyltetrahydrofuran; acetonitrile / 16 h / 20 °C / Inert atmosphere; Large scale reaction

With 1-methyl-1H-imidazole; tetrafluoroboric acid diethyl ether; [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); sodium hypochlorite; tetrakis(triphenylphosphine) palladium⁽⁰⁾; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; Josiphos SL-J₂₁₂-1; hydrogen; sodium ethanolate; potassium acetate; sodium carbonate; In tetrahydrofuran; 2-methyltetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; N,N-dimethyl acetamide; water; acetonitrile; 4.1: Suzuki coupling;

DOI:10.1021/jo102070e

upstream raw materials:

N-[2-chloro-5-(2-methoxyethyl)benzyl]cyclopropanamine

(3'R,4'S)-6-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]-3',4',5',6'-tetrahydro-2'H-[3,4']bipyridinyl-1',3'-dicarboxylic acid 1'-tert-butyl ester

p-toluenesulfonyl chloride

5-bromo-2-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]pyridine

Downstream raw materials:

MK-1597

(3'R,4'S)-6-[2-(2,6-dichloro-4-methyl-phenoxy)ethoxy]-1',2',3',4',5',6'-hexahydro-[3,4']bipyridinyl-3'-carboxylic acid [2-chloro-5-(2-methoxy-ethyl)benzyl]cyclopropylamide acetate

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