3-(4-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)phenyl)propanoic acid

Base Information

• Chemical Name: 3-(4-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)phenyl)propanoic acid
• CAS No.: 1403384-85-9
• Molecular Formula: C₂₇H₂₆N₄O₃
• Molecular Weight: 454.528

Synonyms:3-(4-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)phenyl)propanoic acid

Chemical Property of 3-(4-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)phenyl)propanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(4-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)phenyl)propanoic acid

There total 6 articles about 3-(4-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)phenyl)propanoic acid 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: 52.0%

3-(4-bromophenyl)propionic acid (1643-30-7) + 6-(((2S,4R)-1-acetyl-2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydroquinolin-4-yl)amino)nicotinonitrile (1403384-79-1) → 3-(4-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)phenyl)propanoic acid (1403384-85-9)

Guidance literature:

With potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In ethanol; toluene; at 80 ℃; for 2h;

Reference yield:

1-methylethyl [(2S,4R)-1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (1300031-98-4) → 3-(4-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)phenyl)propanoic acid (1403384-85-9)

Guidance literature:

Multi-step reaction with 4 steps

1: aluminum (III) chloride / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

2: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 2 h / 200 °C / Microwave irradiation; Inert atmosphere

3: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / dimethyl sulfoxide / 2.5 h / 80 °C / Inert atmosphere

4: potassium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene; ethanol / 2 h / 80 °C

With aluminum (III) chloride; potassium acetate; potassium carbonate; N-ethyl-N,N-diisopropylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1-methyl-pyrrolidin-2-one; ethanol; dichloromethane; dimethyl sulfoxide; toluene;

Reference yield:

1-methylethyl {(3S)-3-[(4-bromophenyl)amino]butanoyl}carbamate (1300031-94-0) → 3-(4-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)phenyl)propanoic acid (1403384-85-9)

Guidance literature:

Multi-step reaction with 6 steps

1: sodium tetrahydroborate; magnesium(II) chloride hexahydrate / ethanol; water / 2 h / -10 - 20 °C

2: pyridine / dichloromethane / 16 h / 20 °C / Inert atmosphere

3: aluminum (III) chloride / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

4: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 2 h / 200 °C / Microwave irradiation; Inert atmosphere

5: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / dimethyl sulfoxide / 2.5 h / 80 °C / Inert atmosphere

6: potassium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene; ethanol / 2 h / 80 °C

With pyridine; aluminum (III) chloride; sodium tetrahydroborate; magnesium(II) chloride hexahydrate; potassium acetate; potassium carbonate; N-ethyl-N,N-diisopropylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1-methyl-pyrrolidin-2-one; ethanol; dichloromethane; water; dimethyl sulfoxide; toluene;

upstream raw materials:

3-(4-bromophenyl)propionic acid

6-(((2S,4R)-1-acetyl-2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydroquinolin-4-yl)amino)nicotinonitrile

1-methylethyl [(2S,4R)-1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate

1-methylethyl [(2S,4R)-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate

Downstream raw materials:

3-(4-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1, 2,3,4-tetrahydroquinolin-6-yl)phenyl)-N-(2-(dimethylamino)ethyl)propanamide

3-(4-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1, 2,3,4-tetrahydroquinolin-6-yl)phenyl)-N-(2-hydroxyethyl)propanamide

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