7-(3,5-dimethyl-4-isoxazolyl)-6-(methyloxy)-4-{[(1R)-1-(2-pyridinyl)ethyl]amino}-3-quinolinecarboxamide

Base Information

• Chemical Name: 7-(3,5-dimethyl-4-isoxazolyl)-6-(methyloxy)-4-{[(1R)-1-(2-pyridinyl)ethyl]amino}-3-quinolinecarboxamide
• CAS No.: 1300737-69-2
• Molecular Formula: C₂₃H₂₃N₅O₃
• Molecular Weight: 417.467
• Mol file: 1300737-69-2.mol

Synonyms:

Chemical Property of 7-(3,5-dimethyl-4-isoxazolyl)-6-(methyloxy)-4-{[(1R)-1-(2-pyridinyl)ethyl]amino}-3-quinolinecarboxamide

Chemical Property:

Purity/Quality:

98.5% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-(3,5-dimethyl-4-isoxazolyl)-6-(methyloxy)-4-{[(1R)-1-(2-pyridinyl)ethyl]amino}-3-quinolinecarboxamide

There total 12 articles about 7-(3,5-dimethyl-4-isoxazolyl)-6-(methyloxy)-4-{[(1R)-1-(2-pyridinyl)ethyl]amino}-3-quinolinecarboxamide 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: 72.0%

4-chloro-7-(3,5-dimethyl-4-isoxazolyl)-6-(methyloxy)-3-quinolinecarboxamide (1300031-57-5) + (R)-1-(pyridin-2-yl)ethanamine (27854-90-6,42088-91-5,42732-17-2,45695-03-2) → 7-(3,5-dimethyl-4-isoxazolyl)-6-(methyloxy)-4-{[(1R)-1-(2-pyridinyl)ethyl]amino}-3-quinolinecarboxamide (1300737-69-2)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 120 ℃;

DOI:10.1016/j.bmcl.2012.01.125

Reference yield:

3,5-dimethylisoxazole-4-boronic acid (16114-47-9) → 7-(3,5-dimethyl-4-isoxazolyl)-6-(methyloxy)-4-{[(1R)-1-(2-pyridinyl)ethyl]amino}-3-quinolinecarboxamide (1300737-69-2)

Guidance literature:

Multi-step reaction with 8 steps

1: caesium carbonate / 1,2-dimethoxyethane; water / 4 h / 90 °C / Inert atmosphere

2: palladium on activated charcoal; hydrogen; sodium sulfite / ethanol; ethyl acetate / 24 h

3: 1 h / 130 °C

4: diphenylether / 0.75 h / 255 °C

5: sodium hydroxide / ethanol / Reflux

6: trichlorophosphate / 4 h / Heating

7: ammonium hydroxide / tetrahydrofuran / 0.5 h / Cooling with ice

8: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 120 °C

With ammonium hydroxide; diphenylether; palladium on activated charcoal; hydrogen; caesium carbonate; N-ethyl-N,N-diisopropylamine; sodium hydroxide; sodium sulfite; trichlorophosphate; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; 1,2-dimethoxyethane; ethanol; water; ethyl acetate; 1: Suzuki coupling;

DOI:10.1016/j.bmcl.2012.01.125

Reference yield:

2-iodo-1-methoxy-4-nitrobenzene (5399-03-1) → 7-(3,5-dimethyl-4-isoxazolyl)-6-(methyloxy)-4-{[(1R)-1-(2-pyridinyl)ethyl]amino}-3-quinolinecarboxamide (1300737-69-2)

Guidance literature:

Multi-step reaction with 8 steps

1: caesium carbonate / 1,2-dimethoxyethane; water / 4 h / 90 °C / Inert atmosphere

2: palladium on activated charcoal; hydrogen; sodium sulfite / ethanol; ethyl acetate / 24 h

3: 1 h / 130 °C

4: diphenylether / 0.75 h / 255 °C

5: sodium hydroxide / ethanol / Reflux

6: trichlorophosphate / 4 h / Heating

7: ammonium hydroxide / tetrahydrofuran / 0.5 h / Cooling with ice

8: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 120 °C

With ammonium hydroxide; diphenylether; palladium on activated charcoal; hydrogen; caesium carbonate; N-ethyl-N,N-diisopropylamine; sodium hydroxide; sodium sulfite; trichlorophosphate; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; 1,2-dimethoxyethane; ethanol; water; ethyl acetate; 1: Suzuki coupling;

DOI:10.1016/j.bmcl.2012.01.125

upstream raw materials:

4-chloro-7-(3,5-dimethyl-4-isoxazolyl)-6-(methyloxy)-3-quinolinecarboxamide

(R)-1-(pyridin-2-yl)ethanamine

3,5-dimethylisoxazole-4-boronic acid

2-iodo-1-methoxy-4-nitrobenzene

Downstream raw materials:

I-BET151