trans-N-cyclopropyl-N-({2,3-dichloro-5-[3-(methyloxy)propyl]phenyl}methyl)-4-(1-methyl-2-oxo-1,2-dihydro-4-pyridinyl)-3-piperidinecarboxamide

Base Information

• Chemical Name: trans-N-cyclopropyl-N-({2,3-dichloro-5-[3-(methyloxy)propyl]phenyl}methyl)-4-(1-methyl-2-oxo-1,2-dihydro-4-pyridinyl)-3-piperidinecarboxamide
• CAS No.: 1335221-09-4
• Molecular Formula: C₂₆H₃₃Cl₂N₃O₃
• Molecular Weight: 506.472

Synonyms:

Chemical Property of trans-N-cyclopropyl-N-({2,3-dichloro-5-[3-(methyloxy)propyl]phenyl}methyl)-4-(1-methyl-2-oxo-1,2-dihydro-4-pyridinyl)-3-piperidinecarboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of trans-N-cyclopropyl-N-({2,3-dichloro-5-[3-(methyloxy)propyl]phenyl}methyl)-4-(1-methyl-2-oxo-1,2-dihydro-4-pyridinyl)-3-piperidinecarboxamide

There total 13 articles about trans-N-cyclopropyl-N-({2,3-dichloro-5-[3-(methyloxy)propyl]phenyl}methyl)-4-(1-methyl-2-oxo-1,2-dihydro-4-pyridinyl)-3-piperidinecarboxamide 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:

4-bromo-2-methoxypyridine (100367-39-3) → trans-N-cyclopropyl-N-({2,3-dichloro-5-[3-(methyloxy)propyl]phenyl}methyl)-4-(1-methyl-2-oxo-1,2-dihydro-4-pyridinyl)-3-piperidinecarboxamide (1335221-09-4)

Guidance literature:

Multi-step reaction with 8 steps

1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / propan-1-ol; water / 14 h / 8 °C

2: methanol; magnesium / 2 h / Sonication

3: sodium ethanolate / ethanol / 16 h / 80 °C

4: sodium iodide / acetonitrile / 72 h / 45 °C

5: chiral AD column / ethanol; hexane; isopropyl alcohol / Resolution of racemate

6: water; lithium hydroxide / tetrahydrofuran; methanol / 16 h

7: HATU / N,N-dimethyl-formamide

With methanol; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; water; sodium ethanolate; sodium carbonate; magnesium; HATU; sodium iodide; lithium hydroxide; In tetrahydrofuran; methanol; propan-1-ol; ethanol; hexane; water; N,N-dimethyl-formamide; isopropyl alcohol; acetonitrile; 1: Suzuki coupling;

DOI:10.1016/j.bmcl.2011.05.013

Reference yield:

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-5,6-dihydro-2H-pyridine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (1194488-90-8) → trans-N-cyclopropyl-N-({2,3-dichloro-5-[3-(methyloxy)propyl]phenyl}methyl)-4-(1-methyl-2-oxo-1,2-dihydro-4-pyridinyl)-3-piperidinecarboxamide (1335221-09-4)

Guidance literature:

Multi-step reaction with 8 steps

1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / propan-1-ol; water / 14 h / 8 °C

2: methanol; magnesium / 2 h / Sonication

3: sodium ethanolate / ethanol / 16 h / 80 °C

4: sodium iodide / acetonitrile / 72 h / 45 °C

5: chiral AD column / ethanol; hexane; isopropyl alcohol / Resolution of racemate

6: water; lithium hydroxide / tetrahydrofuran; methanol / 16 h

7: HATU / N,N-dimethyl-formamide

With methanol; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; water; sodium ethanolate; sodium carbonate; magnesium; HATU; sodium iodide; lithium hydroxide; In tetrahydrofuran; methanol; propan-1-ol; ethanol; hexane; water; N,N-dimethyl-formamide; isopropyl alcohol; acetonitrile; 1: Suzuki coupling;

DOI:10.1016/j.bmcl.2011.05.013

Reference yield:

C19H28N2O5 (1315060-85-5) → trans-N-cyclopropyl-N-({2,3-dichloro-5-[3-(methyloxy)propyl]phenyl}methyl)-4-(1-methyl-2-oxo-1,2-dihydro-4-pyridinyl)-3-piperidinecarboxamide (1335221-09-4)

Guidance literature:

Multi-step reaction with 6 steps

1: sodium ethanolate / ethanol / 16 h / 80 °C

2: sodium iodide / acetonitrile / 72 h / 45 °C

3: chiral AD column / ethanol; hexane; isopropyl alcohol / Resolution of racemate

4: water; lithium hydroxide / tetrahydrofuran; methanol / 16 h

5: HATU / N,N-dimethyl-formamide

With water; sodium ethanolate; HATU; sodium iodide; lithium hydroxide; In tetrahydrofuran; methanol; ethanol; hexane; N,N-dimethyl-formamide; isopropyl alcohol; acetonitrile;

DOI:10.1016/j.bmcl.2011.05.013

upstream raw materials:

4-bromo-2-methoxypyridine

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-5,6-dihydro-2H-pyridine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester

1-tert-butyl 3-ethyl 2'-methoxy-5,6-dihydro-4,4'-bipyridine-1,3(2H)-dicarboxylate

C₁₉H₂₈N₂O₅

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