7-(hydroxymethyl)-1-methyl-4-oxo-N-(2-(trifluoromethyl)-4-biphenylyl)-1,4-dihydro-3-quinolinecarboxamide

Base Information

• Chemical Name: 7-(hydroxymethyl)-1-methyl-4-oxo-N-(2-(trifluoromethyl)-4-biphenylyl)-1,4-dihydro-3-quinolinecarboxamide
• CAS No.: 1351945-09-9
• Molecular Formula: C₂₅H₁₉F₃N₂O₃
• Molecular Weight: 452.433
• Mol file: 1351945-09-9.mol

Synonyms:

Chemical Property of 7-(hydroxymethyl)-1-methyl-4-oxo-N-(2-(trifluoromethyl)-4-biphenylyl)-1,4-dihydro-3-quinolinecarboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-(hydroxymethyl)-1-methyl-4-oxo-N-(2-(trifluoromethyl)-4-biphenylyl)-1,4-dihydro-3-quinolinecarboxamide

There total 8 articles about 7-(hydroxymethyl)-1-methyl-4-oxo-N-(2-(trifluoromethyl)-4-biphenylyl)-1,4-dihydro-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: 17.0%

methyl 3-azetidinecarboxylate hydrochloride (100202-39-9) + 7-formyl-1-methyl-4-oxo-N-(2-(trifluoromethyl)biphenyl-4-yl)-1,4-dihydroquinoline-3-carboxamide (1351945-34-0) → 7-(hydroxymethyl)-1-methyl-4-oxo-N-(2-(trifluoromethyl)-4-biphenylyl)-1,4-dihydro-3-quinolinecarboxamide (1351945-09-9) + methyl 1-((1-methyl-4-oxo-3-(2-(trifluoromethyl)biphenyl-4-ylcarbamoyl)-1,4-dihydroquinolin-7-yl)methyl)azetidine-3-carboxylate (1372633-66-3)

Guidance literature:

methyl 3-azetidinecarboxylate hydrochloride; 7-formyl-1-methyl-4-oxo-N-(2-(trifluoromethyl)biphenyl-4-yl)-1,4-dihydroquinoline-3-carboxamide; With acetic acid; triethylamine; In methanol; dichloromethane; at 0 ℃; for 10h;

With sodium cyanoborohydride; at 20 ℃; for 3h;

DOI:10.1021/ml200252b

Reference yield:

2-(trifluoromethyl)biphenyl-4-amine → 7-(hydroxymethyl)-1-methyl-4-oxo-N-(2-(trifluoromethyl)-4-biphenylyl)-1,4-dihydro-3-quinolinecarboxamide (1351945-09-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 17 h / 60 °C

2.1: bis(tri-t-butylphosphine)palladium⁽⁰⁾; cesium fluoride / 1,4-dioxane / 21.5 h / 20 - 80 °C / Inert atmosphere

3.1: sodium periodate; osmium(VIII) oxide / tetrahydrofuran; water / 4.5 h / 20 - 60 °C

4.1: acetic acid; triethylamine / methanol; dichloromethane / 10 h / 0 °C

4.2: 3 h / 20 °C

With sodium periodate; osmium(VIII) oxide; bis(tri-t-butylphosphine)palladium⁽⁰⁾; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; acetic acid; triethylamine; cesium fluoride; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/ml200252b

Reference yield:

ethyl 7-bromo-1-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate → 7-(hydroxymethyl)-1-methyl-4-oxo-N-(2-(trifluoromethyl)-4-biphenylyl)-1,4-dihydro-3-quinolinecarboxamide (1351945-09-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: lithium hydroxide monohydrate / methanol / 1 h / 60 °C

1.2: pH 6 / aq. phosphate buffer

2.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 17 h / 60 °C

3.1: bis(tri-t-butylphosphine)palladium⁽⁰⁾; cesium fluoride / 1,4-dioxane / 21.5 h / 20 - 80 °C / Inert atmosphere

4.1: sodium periodate; osmium(VIII) oxide / tetrahydrofuran; water / 4.5 h / 20 - 60 °C

5.1: acetic acid; triethylamine / methanol; dichloromethane / 10 h / 0 °C

5.2: 3 h / 20 °C

With sodium periodate; osmium(VIII) oxide; bis(tri-t-butylphosphine)palladium⁽⁰⁾; lithium hydroxide monohydrate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; acetic acid; triethylamine; cesium fluoride; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/ml200252b

upstream raw materials:

methyl 3-azetidinecarboxylate hydrochloride

7-formyl-1-methyl-4-oxo-N-(2-(trifluoromethyl)biphenyl-4-yl)-1,4-dihydroquinoline-3-carboxamide

7-bromo-1-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

7-bromo-1-methyl-4-oxo-N-(2-(trifluoromethyl)-4-biphenylyl)-1,4-dihydro-3-quinolinecarboxamide

Refernces